No renderable structure data available
C1CSSC1CCCCCOChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 5-(dithiolan-3-yl)pentan-1-ol |
|---|---|
| IUPAC Name | — |
| CAS Number | 539-55-9 |
| Database ID | 11229306 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
5-(dithiolan-3-yl)pentan-1-ol (CAS 539-55-9) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 11229306
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
9 reactions · 9 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-d0a21c29572b4b51bb3d96ee69cc5f80Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of ethyl 5-(1,2-dithiolan-3-yl)pentanoate in 40 ml of anhydrous tetrahydrofuran was added dropwise, whilst cooling with ice and sodium chloride, to a suspension of 3.34 g of lithium aluminum hydride in 150 ml of anhydrous tetrahydrofuran. The resulting mixture was stirred at room temperature for 3 hours and 30 minutes. Sodium sulfate decahydrate was then added, whilst cooling with ice and sodium chloride, to the reaction mixture, and then the mixture was stirred at room temperature for 3 hours. The reaction mixture was allowed to stand overnight at room temperature, and then insoluble matter was filtered off using a Celite (trade mark) filter aid. The solvent was removed from the filtrate by distillation under reduced pressure. 50 ml of methanol, 25 ml of a 1 N aqueous solution of sodium hydroxide and 10 ml of 2 N aqueous hydrochloric acid were then added to the residue. Air was then blown into the resulting mixture. Five drops of a 1% aqueous solution of ferric chloride were added dropwise to the reaction mixture, and then the mixture was stirred at room temperature for one hour. The reaction mixture was allowed to stand overnight at room temperature, and then the solvent was removed by distillation under reduced pressure. Water was added to the residue, after which it was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. Ethyl acetate was removed from the extract by distillation under reduced pressure, and the residue was subjected to silica gel column chromatography, using 1:2 and 1:1 by volume mixtures of ethyl acetate and hexane as eluent. The solvent was removed from the resulting eluate by distillation under reduced pressure, and 30 ml of toluene were added to the residue. 1 ml was taken from the resulting solution, and the solvent was removed by distillation under reduced pressure, to give 0.13 g of the title compound as a yellow oil having an Rf value of 0.39 (silica gel thin layer chromatography; using a 1:1 by volume mixture of ethyl acetate and hexane as the eluent). the mixture was stirred at room temperature for 3 hours to stand overnight at room temperature insoluble matter was filtered off filter aid The solvent was removed from the filtrate by distillation under reduced pressure 50 ml of methanol, 25 ml of a 1 N aqueous solution of sodium hydroxide and 10 ml of 2 N aqueous hydrochloric acid were then added to the residue Five drops of a 1% aqueous solution of ferric chloride were added dropwise to the reaction mixture the mixture was stirred at room temperature for one hour to stand overnight at room temperature the solvent was removed by distillation under reduced pressure Water was added to the residue after which it was extracted with ethyl acetate The extract was washed with a saturated aqueous solution of sodium chloride dried over anhydrous sodium sulfate Ethyl acetate was removed from the extract by distillation under reduced pressure The solvent was removed from the resulting eluate by distillation under reduced pressure, and 30 ml of toluene were added to the residue the solvent was removed by distillation under reduced pressure
Source ID: ord-b74045cc7a874941955fd3189cbb9585Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of ethyl 5-(1,2-dithiolan-3-yl)pentanoate in 40 ml of anhydrous tetrahydrofuran was added dropwise, whilst cooling with ice and sodium chloride, to a suspension of 3.34 g of lithium aluminum hydride in 150 ml of anhydrous tetrahydrofuran. The resulting mixture was stirred at room temperature for 3 hours and 30 minutes. Sodium sulfate decahydrate was then added, whilst cooling with ice and sodium chloride, to the reaction mixture, and then the mixture was stirred at room temperature for 3 hours. The reaction mixture was allowed to stand overnight at room temperature, and then insoluble matter was filtered off using a Celite (trade mark) filter aid. The solvent was removed from the filtrate by distillation under reduced pressure. 50 ml of methanol, 25 ml of a 1 N aqueous solution of sodium hydroxide and 10 ml of 2 N aqueous hydrochloric acid were then added to the residue. Air was then blown into the resulting mixture. Five drops of a 1% aqueous solution of ferric chloride were added dropwise to the reaction mixture, and then the mixture was stirred at room temperature for one hour. The reaction mixture was allowed to stand overnight at room temperature, and then the solvent was removed by distillation under reduced pressure. Water was added to the residue, after which it was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. Ethyl acetate was removed from the extract by distillation under reduced pressure, and the residue was subjected to silica gel column chromatography, using 1:2 and 1:1 by volume mixtures of ethyl acetate and hexane as eluent. The solvent was removed from the resulting eluate by distillation under reduced pressure, and 30 ml of toluene were added to the residue. 1 ml was taken from the resulting solution, and the solvent was removed by distillation under reduced pressure, to give 0.13 g of the title compound as a yellow oil having an Rf value of 0.39 (silica gel thin layer chromatography; using a 1:1 by volume mixture of ethyl acetate and hexane as the eluent). the mixture was stirred at room temperature for 3 hours to stand overnight at room temperature insoluble matter was filtered off filter aid The solvent was removed from the filtrate by distillation under reduced pressure 50 ml of methanol, 25 ml of a 1 N aqueous solution of sodium hydroxide and 10 ml of 2 N aqueous hydrochloric acid were then added to the residue Five drops of a 1% aqueous solution of ferric chloride were added dropwise to the reaction mixture the mixture was stirred at room temperature for one hour to stand overnight at room temperature the solvent was removed by distillation under reduced pressure Water was added to the residue after which it was extracted with ethyl acetate The extract was washed with a saturated aqueous solution of sodium chloride dried over anhydrous sodium sulfate Ethyl acetate was removed from the extract by distillation under reduced pressure The solvent was removed from the resulting eluate by distillation under reduced pressure, and 30 ml of toluene were added to the residue the solvent was removed by distillation under reduced pressure
Source ID: ord-b74045cc7a874941955fd3189cbb9585Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3.25 ml of dimethyl azodicarboxylate were added dropwise to a solution of 5.77 g of triphenylphosphine in 20 ml of tetrahydrofuran, whilst ice-cooling, and then the mixture was stirred at room temperature for 30 minutes. 3.24 g of phthalimide were then added to the reaction mixture, after which a mixture of 20 mmol of 5-(1,2-dithiolan-3-yl)pentanol (prepared as described in Preparation 1) in 30 ml of toluene and 10 ml of tetrahydrofuran was added dropwise, and the mixture was stirred at room temperature for one hour. The reaction mixture was allowed to stand overnight at room temperature, after which 1.57 g of triphenylphosphine and 0.89 ml of dimethyl azodicarboxylate were added. The resulting mixture was stirred at room temperature for 7 hours and 30 minutes. 0.88 g of phthalimide, 1.57 g of triphenylphosphine and 0.89 ml of dimethyl azodicarboxylate were then added to the reaction mixture. The reaction mixture was allowed to stand at room temperature for 4 days. At the end of this time, the solvent was removed from the reaction mixture by distillation under reduced pressure, and the residue was subjected to silica gel column chromatography, using 1:6 and 1:4 by volume mixtures of ethyl acetate and hexane as eluent. The solvent was removed from the eluate by distillation under reduced pressure, and 30 ml of toluene were added to the residue. 1 ml of the resulting mixture was weighed, and the solvent was removed from it by distillation under reduced pressure, to give 165 mg of the title compound as an orange oil having an Rf value of 0.35 (silica gel thin layer chromatography; using a 1:4 by volume mixture of ethyl acetate and hexane as the developing solvent). cooling was added dropwise the mixture was stirred at room temperature for one hour to stand overnight at room temperature The resulting mixture was stirred at room temperature for 7 hours and 30 minutes to stand at room temperature for 4 days At the end of this time, the solvent was removed from the reaction mixture by distillation under reduced pressure The solvent was removed from the eluate by distillation under reduced pressure, and 30 ml of toluene were added to the residue the solvent was removed from it by distillation under reduced pressure
Source ID: ord-39f90693d8504cb0983b31f78bfc71b5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of ethyl 5-(1,2-dithiolan-3-yl)pentanoate in 40 ml of anhydrous tetrahydrofuran was added dropwise, whilst cooling with ice and sodium chloride, to a suspension of 3.34 g of lithium aluminum hydride in 150 ml of anhydrous tetrahydrofuran. The resulting mixture was stirred at room temperature for 3 hours and 30 minutes. Sodium sulfate decahydrate was then added, whilst cooling with ice and sodium chloride, to the reaction mixture, and then the mixture was stirred at room temperature for 3 hours. The reaction mixture was allowed to stand overnight at room temperature, and then insoluble matter was filtered off using a Celite (trade mark) filter aid. The solvent was removed from the filtrate by distillation under reduced pressure. 50 ml of methanol, 25 ml of a 1 N aqueous solution of sodium hydroxide and 10 ml of 2 N aqueous hydrochloric acid were then added to the residue. Air was then blown into the resulting mixture. Five drops of a 1% aqueous solution of ferric chloride were added dropwise to the reaction mixture, and then the mixture was stirred at room temperature for one hour. The reaction mixture was allowed to stand overnight at room temperature, and then the solvent was removed by distillation under reduced pressure. Water was added to the residue, after which it was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. Ethyl acetate was removed from the extract by distillation under reduced pressure, and the residue was subjected to silica gel column chromatography, using 1:2 and 1:1 by volume mixtures of ethyl acetate and hexane as eluent. The solvent was removed from the resulting eluate by distillation under reduced pressure, and 30 ml of toluene were added to the residue. 1 ml was taken from the resulting solution, and the solvent was removed by distillation under reduced pressure, to give 0.13 g of the title compound as a yellow oil having an Rf value of 0.39 (silica gel thin layer chromatography; using a 1:1 by volume mixture of ethyl acetate and hexane as the eluent). the mixture was stirred at room temperature for 3 hours to stand overnight at room temperature insoluble matter was filtered off filter aid The solvent was removed from the filtrate by distillation under reduced pressure 50 ml of methanol, 25 ml of a 1 N aqueous solution of sodium hydroxide and 10 ml of 2 N aqueous hydrochloric acid were then added to the residue Five drops of a 1% aqueous solution of ferric chloride were added dropwise to the reaction mixture the mixture was stirred at room temperature for one hour to stand overnight at room temperature the solvent was removed by distillation under reduced pressure Water was added to the residue after which it was extracted with ethyl acetate The extract was washed with a saturated aqueous solution of sodium chloride dried over anhydrous sodium sulfate Ethyl acetate was removed from the extract by distillation under reduced pressure The solvent was removed from the resulting eluate by distillation under reduced pressure, and 30 ml of toluene were added to the residue the solvent was removed by distillation under reduced pressure
Source ID: ord-f00aaea46ee44b7bbb73aba6bdee204bConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-d0a21c29572b4b51bb3d96ee69cc5f80Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of ethyl 5-(1,2-dithiolan-3-yl)pentanoate in 40 ml of anhydrous tetrahydrofuran was added dropwise, whilst cooling with ice and sodium chloride, to a suspension of 3.34 g of lithium aluminum hydride in 150 ml of anhydrous tetrahydrofuran. The resulting mixture was stirred at room temperature for 3 hours and 30 minutes. Sodium sulfate decahydrate was then added, whilst cooling with ice and sodium chloride, to the reaction mixture, and then the mixture was stirred at room temperature for 3 hours. The reaction mixture was allowed to stand overnight at room temperature, and then insoluble matter was filtered off using a Celite (trade mark) filter aid. The solvent was removed from the filtrate by distillation under reduced pressure. 50 ml of methanol, 25 ml of a 1 N aqueous solution of sodium hydroxide and 10 ml of 2 N aqueous hydrochloric acid were then added to the residue. Air was then blown into the resulting mixture. Five drops of a 1% aqueous solution of ferric chloride were added dropwise to the reaction mixture, and then the mixture was stirred at room temperature for one hour. The reaction mixture was allowed to stand overnight at room temperature, and then the solvent was removed by distillation under reduced pressure. Water was added to the residue, after which it was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. Ethyl acetate was removed from the extract by distillation under reduced pressure, and the residue was subjected to silica gel column chromatography, using 1:2 and 1:1 by volume mixtures of ethyl acetate and hexane as eluent. The solvent was removed from the resulting eluate by distillation under reduced pressure, and 30 ml of toluene were added to the residue. 1 ml was taken from the resulting solution, and the solvent was removed by distillation under reduced pressure, to give 0.13 g of the title compound as a yellow oil having an Rf value of 0.39 (silica gel thin layer chromatography; using a 1:1 by volume mixture of ethyl acetate and hexane as the eluent). the mixture was stirred at room temperature for 3 hours to stand overnight at room temperature insoluble matter was filtered off filter aid The solvent was removed from the filtrate by distillation under reduced pressure 50 ml of methanol, 25 ml of a 1 N aqueous solution of sodium hydroxide and 10 ml of 2 N aqueous hydrochloric acid were then added to the residue Five drops of a 1% aqueous solution of ferric chloride were added dropwise to the reaction mixture the mixture was stirred at room temperature for one hour to stand overnight at room temperature the solvent was removed by distillation under reduced pressure Water was added to the residue after which it was extracted with ethyl acetate The extract was washed with a saturated aqueous solution of sodium chloride dried over anhydrous sodium sulfate Ethyl acetate was removed from the extract by distillation under reduced pressure The solvent was removed from the resulting eluate by distillation under reduced pressure, and 30 ml of toluene were added to the residue the solvent was removed by distillation under reduced pressure
Source ID: ord-b74045cc7a874941955fd3189cbb9585Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3.25 ml of dimethyl azodicarboxylate were added dropwise to a solution of 5.77 g of triphenylphosphine in 20 ml of tetrahydrofuran, whilst ice-cooling, and then the mixture was stirred at room temperature for 30 minutes. 3.24 g of phthalimide were then added to the reaction mixture, after which a mixture of 20 mmol of 5-(1,2-dithiolan-3-yl)pentanol (prepared as described in Preparation 1) in 30 ml of toluene and 10 ml of tetrahydrofuran was added dropwise, and the mixture was stirred at room temperature for one hour. The reaction mixture was allowed to stand overnight at room temperature, after which 1.57 g of triphenylphosphine and 0.89 ml of dimethyl azodicarboxylate were added. The resulting mixture was stirred at room temperature for 7 hours and 30 minutes. 0.88 g of phthalimide, 1.57 g of triphenylphosphine and 0.89 ml of dimethyl azodicarboxylate were then added to the reaction mixture. The reaction mixture was allowed to stand at room temperature for 4 days. At the end of this time, the solvent was removed from the reaction mixture by distillation under reduced pressure, and the residue was subjected to silica gel column chromatography, using 1:6 and 1:4 by volume mixtures of ethyl acetate and hexane as eluent. The solvent was removed from the eluate by distillation under reduced pressure, and 30 ml of toluene were added to the residue. 1 ml of the resulting mixture was weighed, and the solvent was removed from it by distillation under reduced pressure, to give 165 mg of the title compound as an orange oil having an Rf value of 0.35 (silica gel thin layer chromatography; using a 1:4 by volume mixture of ethyl acetate and hexane as the developing solvent). cooling was added dropwise the mixture was stirred at room temperature for one hour to stand overnight at room temperature The resulting mixture was stirred at room temperature for 7 hours and 30 minutes to stand at room temperature for 4 days At the end of this time, the solvent was removed from the reaction mixture by distillation under reduced pressure The solvent was removed from the eluate by distillation under reduced pressure, and 30 ml of toluene were added to the residue the solvent was removed from it by distillation under reduced pressure
Source ID: ord-39f90693d8504cb0983b31f78bfc71b5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of ethyl 5-(1,2-dithiolan-3-yl)pentanoate in 40 ml of anhydrous tetrahydrofuran was added dropwise, whilst cooling with ice and sodium chloride, to a suspension of 3.34 g of lithium aluminum hydride in 150 ml of anhydrous tetrahydrofuran. The resulting mixture was stirred at room temperature for 3 hours and 30 minutes. Sodium sulfate decahydrate was then added, whilst cooling with ice and sodium chloride, to the reaction mixture, and then the mixture was stirred at room temperature for 3 hours. The reaction mixture was allowed to stand overnight at room temperature, and then insoluble matter was filtered off using a Celite (trade mark) filter aid. The solvent was removed from the filtrate by distillation under reduced pressure. 50 ml of methanol, 25 ml of a 1 N aqueous solution of sodium hydroxide and 10 ml of 2 N aqueous hydrochloric acid were then added to the residue. Air was then blown into the resulting mixture. Five drops of a 1% aqueous solution of ferric chloride were added dropwise to the reaction mixture, and then the mixture was stirred at room temperature for one hour. The reaction mixture was allowed to stand overnight at room temperature, and then the solvent was removed by distillation under reduced pressure. Water was added to the residue, after which it was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. Ethyl acetate was removed from the extract by distillation under reduced pressure, and the residue was subjected to silica gel column chromatography, using 1:2 and 1:1 by volume mixtures of ethyl acetate and hexane as eluent. The solvent was removed from the resulting eluate by distillation under reduced pressure, and 30 ml of toluene were added to the residue. 1 ml was taken from the resulting solution, and the solvent was removed by distillation under reduced pressure, to give 0.13 g of the title compound as a yellow oil having an Rf value of 0.39 (silica gel thin layer chromatography; using a 1:1 by volume mixture of ethyl acetate and hexane as the eluent). the mixture was stirred at room temperature for 3 hours to stand overnight at room temperature insoluble matter was filtered off filter aid The solvent was removed from the filtrate by distillation under reduced pressure 50 ml of methanol, 25 ml of a 1 N aqueous solution of sodium hydroxide and 10 ml of 2 N aqueous hydrochloric acid were then added to the residue Five drops of a 1% aqueous solution of ferric chloride were added dropwise to the reaction mixture the mixture was stirred at room temperature for one hour to stand overnight at room temperature the solvent was removed by distillation under reduced pressure Water was added to the residue after which it was extracted with ethyl acetate The extract was washed with a saturated aqueous solution of sodium chloride dried over anhydrous sodium sulfate Ethyl acetate was removed from the extract by distillation under reduced pressure The solvent was removed from the resulting eluate by distillation under reduced pressure, and 30 ml of toluene were added to the residue the solvent was removed by distillation under reduced pressure
Source ID: ord-f00aaea46ee44b7bbb73aba6bdee204bPubChem References
These sources are listed in the compound's public database record.
Request a Quote
Send the required specification, quantity, destination and intended use. The CATO team will review availability and respond.