No renderable structure data available
CCCCOS(=O)(=O)C1CC1Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | butyl cyclopropanesulfonate |
|---|---|
| IUPAC Name | — |
| CAS Number | 83635-12-5 |
| Database ID | 10464888 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
butyl cyclopropanesulfonate (CAS 83635-12-5) 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 10464888
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-ddbf71f53e704add9c736b0601df9d46Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-4a3583cde0ee4da8ad5149cb56807437Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-9a5bf87190174bfc8813fa056d3acbe3Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 1-butyl cyclopropanesulfonate (4.8 g, 24.9 mmol) in THF at −78° C. was added simultaneously butyllithium solution (15.6 ml, 24.9 mmol, 1.6M, THF) and allyl iodide (24.9 mmol) under nitrogen atmosphere. The reaction mixture was stirred 2 hours at −78° C. and 3 hours at room temperature. The volatiles were evaporated under reduced pressure and the residue extracted with CH2Cl2 (100 ml). The extract was washed with water, dried (MgSO4) and evaporated. The residue was purified over silica gel chromatography (eluants: hexane/CH2Cl2) to obtain the titled product (3.75 g, 69.0%) as a colorless oil. 1H NMR (300 MHz, CDCl3): δ 5.6 (m, 1H), 5.13-5.08 (t, 2H), 4.21 (t, 2H), 2.65 (d, 2H), 1.7 (m, 2H), 1.4 (m, 4H), 0.93 (m, 5H). The volatiles were evaporated under reduced pressure the residue extracted with CH2Cl2 (100 ml) The extract was washed with water dried (MgSO4) evaporated The residue was purified over silica gel chromatography (eluants: hexane/CH2Cl2)
Source ID: ord-6417b1cd76bc42e48b364fbb7fefbe73Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Cyclopropanesulfonyl chloride (5 g, 35 mmol, 1 eq) was dissolved in an excess BuOH (20 ml), the reaction mixture was cooled at −10° C. and pyridine (5.8 mL, 70 mmol, 2 eq) was slowly added dropwise. The mixture was slowly warmed at room temperature and stirred overnight. The solvent was removed under reduced pressure and the resulting white solid was dissolved in CHCl3. The organic phase was washed with water, brine and dried (MgSO4) and concentrated to give an oil (4.8 g, 24.9 mmol, 71%). 1H NMR (300 MHz, CDCl3): δ 4.25 (t, 2H), 2.46 (m, 1H), 1.74 (m, 2H), 1.45 (m, 2H), 1.25 (dd, 2H), 1.09 (dd, 2H), 0.93 (t, 3H). The mixture was slowly warmed at room temperature The solvent was removed under reduced pressure the resulting white solid was dissolved in CHCl3 The organic phase was washed with water, brine dried (MgSO4) concentrated
Source ID: ord-1f8bb632d04645afac2b52a7c32e508cConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 1-Butyl cyclopropanesulfonate (1 g, 5.58 mmol) in THF (15 ml) butyllithium solution (3.84 ml, 6.14 mmol, 1.6M, THF) was slowly added at −78° C. under nitrogen atmosphere. After 15 minutes MeI (0.72 ml, 11.16 mmol) was added and the solution was allowed to warm to 0° C. and quenched with water (1 ml). The volatiles evaporated under reduced pressure and the residue extracted with CH2Cl2 (100 ml). The extract was washed with water, dried (MgSO4) and evaporated. The residue was purified over silica gel chromatography (eluants: hexane/CH2Cl2) to obtain the titled product (0.59 g, 55.0%) as a colorless oil. 1H NMR (300 MHz, CDCl3)) δ 0.84 (m, 2H), 0.95 (t, J=7.2 Hz, 3H), 1.43 (m, 4H), 1.53 (s, 3H), 1.74 (m, 2H), 4.21 ((t, J=6.6 Hz, 2H). quenched with water (1 ml) The volatiles evaporated under reduced pressure the residue extracted with CH2Cl2 (100 ml) The extract was washed with water dried (MgSO4) evaporated The residue was purified over silica gel chromatography (eluants: hexane/CH2Cl2)
Source ID: ord-0d37736513e04b2488d60f6f9ee6e184Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Solutions of 1-butyl 3-chloro-1-propanesulfonate (4.6 g, 21.39 mmol in 25 ml THF) and of butyllithium (14.7 ml, 23.53 mmol, 1.6M, THF) were simultaneously added to THF (150 ml) at −78° C. under nitrogen atmosphere. The solution was allowed to warm to 0° C. and then quenched with water (2 ml). The volatiles evaporated under reduced pressure and the residue extracted with CH2Cl2 (150 ml). The extract was washed with water and dried (MgSO4) and evaporated to give crude desired product (3.23 g, 78.22%) in almost pure form as pale yellow oil which was used for next step without further purification. 1H NMR (300 MHz, CDCl3) δ 0.94 (t, J=7.5 Hz, 3H), 1.07 (m, 2H), 1.25 (m, 2H), 1.45 (sextet, 2H), 1.74 (quintet, 2H), 2.45 (heptet, 1H), 4.23 (t, J=6.6 Hz, 2H). quenched with water (2 ml) The volatiles evaporated under reduced pressure the residue extracted with CH2Cl2 (150 ml) The extract was washed with water dried (MgSO4) evaporated
Source ID: ord-a93f77e2e6224708a4ae944e519b425aConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-ddbf71f53e704add9c736b0601df9d46Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 1-butyl cyclopropanesulfonate (4.8 g, 24.9 mmol) in THF at −78° C. was added simultaneously butyllithium solution (15.6 ml, 24.9 mmol, 1.6M, THF) and allyl iodide (24.9 mmol) under nitrogen atmosphere. The reaction mixture was stirred 2 hours at −78° C. and 3 hours at room temperature. The volatiles were evaporated under reduced pressure and the residue extracted with CH2Cl2 (100 ml). The extract was washed with water, dried (MgSO4) and evaporated. The residue was purified over silica gel chromatography (eluants: hexane/CH2Cl2) to obtain the titled product (3.75 g, 69.0%) as a colorless oil. 1H NMR (300 MHz, CDCl3): δ 5.6 (m, 1H), 5.13-5.08 (t, 2H), 4.21 (t, 2H), 2.65 (d, 2H), 1.7 (m, 2H), 1.4 (m, 4H), 0.93 (m, 5H). The volatiles were evaporated under reduced pressure the residue extracted with CH2Cl2 (100 ml) The extract was washed with water dried (MgSO4) evaporated The residue was purified over silica gel chromatography (eluants: hexane/CH2Cl2)
Source ID: ord-2b7c585bf0044652a467c0cd45b55bd2Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 1-butyl cyclopropanesulfonate (4.8 g, 24.9 mmol) in THF at −78° C. was added simultaneously butyllithium solution (15.6 ml, 24.9 mmol, 1.6M, THF) and allyl iodide (24.9 mmol) under nitrogen atmosphere. The reaction mixture was stirred 2 hours at −78° C. and 3 hours at room temperature. The volatiles were evaporated under reduced pressure and the residue extracted with CH2Cl2 (100 ml). The extract was washed with water, dried (MgSO4) and evaporated. The residue was purified over silica gel chromatography (eluants: hexane/CH2Cl2) to obtain the titled product (3.75 g, 69.0%) as a colorless oil. 1H NMR (300 MHz, CDCl3): δ 5.6 (m, 1H), 5.13-5.08 (t, 2H), 4.21 (t, 2H), 2.65 (d, 2H), 1.7 (m, 2H), 1.4 (m, 4H), 0.93 (m, 5H). The volatiles were evaporated under reduced pressure the residue extracted with CH2Cl2 (100 ml) The extract was washed with water dried (MgSO4) evaporated The residue was purified over silica gel chromatography (eluants: hexane/CH2Cl2)
Source ID: ord-2b7c585bf0044652a467c0cd45b55bd2Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Cyclopropanesulfonyl chloride (5 g, 35 mmol, 1 eq) was dissolved in an excess BuOH (20 ml), the reaction mixture was cooled at −10° C. and pyridine (5.8 mL, 70 mmol, 2 eq) was slowly added dropwise. The mixture was slowly warmed at room temperature and stirred overnight. The solvent was removed under reduced pressure and the resulting white solid was dissolved in CHCl3. The organic phase was washed with water, brine and dried (MgSO4) and concentrated to give an oil (4.8 g, 24.9 mmol, 71%). 1H NMR (300 MHz, CDCl3): δ 4.25 (t, 2H), 2.46 (m, 1H), 1.74 (m, 2H), 1.45 (m, 2H), 1.25 (dd, 2H), 1.09 (dd, 2H), 0.93 (t, 3H). The mixture was slowly warmed at room temperature The solvent was removed under reduced pressure the resulting white solid was dissolved in CHCl3 The organic phase was washed with water, brine dried (MgSO4) concentrated
Source ID: ord-3f0c56fe5db740a786573f8eb5bf5070Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Cyclopropanesulfonyl chloride (5 g, 35 mmol, 1 eq) was dissolved in an excess BuOH (20 ml), the reaction mixture was cooled at −10° C. and pyridine (5.8 mL, 70 mmol, 2 eq) was slowly added dropwise. The mixture was slowly warmed at room temperature and stirred overnight. The solvent was removed under reduced pressure and the resulting white solid was dissolved in CHCl3. The organic phase was washed with water, brine and dried (MgSO4) and concentrated to give an oil (4.8 g, 24.9 mmol, 71%). 1H NMR (300 MHz, CDCl3): δ 4.25 (t, 2H), 2.46 (m, 1H), 1.74 (m, 2H), 1.45 (m, 2H), 1.25 (dd, 2H), 1.09 (dd, 2H), 0.93 (t, 3H). The mixture was slowly warmed at room temperature The solvent was removed under reduced pressure the resulting white solid was dissolved in CHCl3 The organic phase was washed with water, brine dried (MgSO4) concentrated
Source ID: ord-3f0c56fe5db740a786573f8eb5bf5070PubChem References
These sources are listed in the compound's public database record.
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