No renderable structure data available
C1CC(=O)CCC1CCOCC2=CC=CC=C2Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 4-(2-phenylmethoxyethyl)cyclohexan-1-one |
|---|---|
| IUPAC Name | — |
| CAS Number | 628731-60-2 |
| Database ID | 21879605 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
4-(2-phenylmethoxyethyl)cyclohexan-1-one (CAS 628731-60-2) 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 21879605
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-101e827fe20b4c59ab05911942adc855Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-c8ea6790595e49d6b35af45cbc465d3fConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of LDA (33 ml, 1.5 M in Et2O) in THF (50 mL) at −78° C. was treated with 4-(2-benzyloxy-ethyl)-cyclohexanone (9.5 g, 40.2 mmol). The mixture was warmed to 0° C. over 30 minutes before re-cooling to −78° C. and adding HMPA (7 mL). Methyl cyanoformate (4.1 mL, 85 mmol) was added, and the mixture stirred for 15 minutes before aqueous quench and work-up. The product was purified by chromatography on SiO2 with 10% EtOAc:Hx. 5-(2-Benzyloxy-ethyl)-2-oxo-cyclohexanecarboxylic acid methyl ester was isolated, 5.8 g (49%), and reduced with an equivalent of NaBH4 in MeOH at −10° C. The alcohol. (Intermediate R2 above) was purified by chromatography on SiO2 with 30 to 50% EtOAC:Hx. (˜90% yield). before re-cooling to −78° C. before aqueous quench The product was purified by chromatography on SiO2 with 10% EtOAc
Source ID: ord-be444c2f2d01459baf7556cc2e1137fcConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of LDA (33 ml, 1.5 M in Et2O) in THF (50 mL) at −78° C. was treated with 4-(2-benzyloxy-ethyl)-cyclohexanone (9.5 g, 40.2 mmol). The mixture was warmed to 0° C. over 30 minutes before re-cooling to −78° C. and adding HMPA (7 mL). Methyl cyanoformate (4.1 mL, 85 mmol) was added, and the mixture stirred for 15 minutes before aqueous quench and work-up. The product was purified by chromatography on SiO2 with 10% EtOAc:Hx. 5-(2-Benzyloxy-ethyl)-2-oxo-cyclohexanecarboxylic acid methyl ester was isolated, 5.8 g (49%), and reduced with an equivalent of NaBH4 in MeOH at −10° C. The alcohol. (Intermediate R2 above) was purified by chromatography on SiO2 with 30 to 50% EtOAC:Hx. (˜90% yield). before re-cooling to −78° C. before aqueous quench The product was purified by chromatography on SiO2 with 10% EtOAc
Source ID: ord-be444c2f2d01459baf7556cc2e1137fcConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of LDA (33 ml, 1.5 M in Et2O) in THF (50 mL) at −78° C. was treated with 4-(2-benzyloxy-ethyl)-cyclohexanone (9.5 g, 40.2 mmol). The mixture was warmed to 0° C. over 30 minutes before re-cooling to −78° C. and adding HMPA (7 mL). Methyl cyanoformate (4.1 mL, 85 mmol) was added, and the mixture stirred for 15 minutes before aqueous quench and work-up. The product was purified by chromatography on SiO2 with 10% EtOAc:Hx. 5-(2-Benzyloxy-ethyl)-2-oxo-cyclohexanecarboxylic acid methyl ester was isolated, 5.8 g (49%), and reduced with an equivalent of NaBH4 in MeOH at −10° C. The alcohol (Intermediate R2 above) was purified by chromatography on SiO2 with 30 to 50% EtOAC:Hx. (˜90% yield). before re-cooling to −78° C. before aqueous quench The product was purified by chromatography on SiO2 with 10% EtOAc
Source ID: ord-6709a8ce567c4ae0929308f27f208a73Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of LDA (33 ml, 1.5 M in Et2O) in THF (50 mL) at −78° C. was treated with 4-(2-benzyloxy-ethyl)-cyclohexanone (9.5 g, 40.2 mmol). The mixture was warmed to 0° C. over 30 minutes before re-cooling to −78° C. and adding HMPA (7 mL). Methyl cyanoformate (4.1 mL, 85 mmol) was added, and the mixture stirred for 15 minutes before aqueous quench and work-up. The product was purified by chromatography on SiO2 with 10% EtOAc:Hx. 5-(2-Benzyloxy-ethyl)-2-oxo-cyclohexanecarboxylic acid methyl ester was isolated, 5.8 g (49%), and reduced with an equivalent of NaBH4 in MeOH at −10° C. The alcohol (Intermediate R2 above) was purified by chromatography on SiO2 with 30 to 50% EtOAC:Hx. (˜90% yield). before re-cooling to −78° C. before aqueous quench The product was purified by chromatography on SiO2 with 10% EtOAc
Source ID: ord-8d84dc565ff9450e9f378322146b8a53Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of LDA (33 ml, 1.5 M in Et2O) in THF (50 mL) at −78° C. was treated with 4-(2-benzyloxy-ethyl)-cyclohexanone (9.5 g, 40.2 mmol). The mixture was warmed to 0° C. over 30 m before re-cooling to −78° C. and adding HMPA (7 mL). Methyl cyanoformate (4.1 mL, 85 mmol) was added and the mixture was stirred for 15 m before aqueous quench and work-up. The product was purified by chromatography on SiO2 with 10% EtOAc:Hx. 5-(2-Benzyloxy-ethyl)-2-oxo-cyclohexanecarboxylic acid methyl ester was isolated, 5.8 g (49%) and reduced with an equivalent of NaBH4 in MeOH at −10° C. to provide the alcohol (Intermediate R2). Intermediate R2 was purified by chromatography on SiO2 with 30 to 50% EtOAC:Hx. (˜90% yield). before re-cooling to −78° C. before aqueous quench The product was purified by chromatography on SiO2 with 10% EtOAc
Source ID: ord-e0ace1a8d71f445bae189e56a1ef1c6eConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of LDA (33 ml, 1.5 M in Et2O) in THF (50 mL) at −78° C. was treated with 4-(2-benzyloxy-ethyl)-cyclohexanone (9.5 g, 40.2 mmol). The mixture was warmed to 0° C. over 30 m before re-cooling to −78° C. and adding HMPA (7 mL). Methyl cyanoformate (4.1 mL, 85 mmol) was added and the mixture was stirred for 15 m before aqueous quench and work-up. The product was purified by chromatography on SiO2 with 10% EtOAc:Hx. 5-(2-Benzyloxy-ethyl)-2-oxo-cyclohexanecarboxylic acid methyl ester was isolated, 5.8 g (49%) and reduced with an equivalent of NaBH4 in MeOH at −10° C. to provide the alcohol (Intermediate R2). Intermediate R2 was purified by chromatography on SiO2 with 30 to 50% EtOAC:Hx. (˜90% yield). before re-cooling to −78° C. before aqueous quench The product was purified by chromatography on SiO2 with 10% EtOAc
Source ID: ord-e0ace1a8d71f445bae189e56a1ef1c6eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 8-(2-Benzyloxy-ethyl)-1,4-dioxa-spiro[4.5]decane (Intermediate R1, 1.02 g, 3.70 mmol) (obtainable as described in the publication by Ciufolini et. al. J. Amer. Chem. Soc. 1991, 113, 8016, incorporated herein by reference) was dissolved in acetone (100 mL): H2O (5 mL) and reacted with TsOH (140 mg, 0.74 mmol) at 45° C. for 5 h. After a standard aqueous work-up the material was purified by chromatography on SiO2 to give 4-(2-benzyloxy-ethyl)-cyclohexanone as a colorless oil (97%). After a standard aqueous work-up the material was purified by chromatography on SiO2
Source ID: ord-1586ff7051ac4306869291cddfc9f239Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of LDA (33 ml, 1.5 M in Et2O) in THF (50 mL) at −78° C. was treated with 4-(2-benzyloxy-ethyl)-cyclohexanone (9.5 g, 40.2 mmol). The mixture was warmed to 0° C. over 30 min. before re-cooling to −78° C. and adding HMPA (7 mL). Methyl cyanoformate (CNCO2Me, 4.1 mL, 85 mmol) was added and the mixture was stirred for 15 m before aqueous quench and work-up. The product was purified by chromatography on SiO2 with 10% EtOAc:Hx. 5-(2-Benzyloxy-ethyl)-2-oxo-) cyclohexanecarboxylic acid methyl ester was isolated, 5.8 g (49%). before re-cooling to −78° C. before aqueous quench The product was purified by chromatography on SiO2 with 10% EtOAc
Source ID: ord-204d400862874487a87f3b9e7557ecf1Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 8-(2-Benzyloxy-ethyl)-1,4-dioxa-spiro[4.5]decane (Intermediate K1, 1.02 g, 3.70 mmol) (prepared in accordance with the publication Ciufolini et. al. J. Amer. Chem. Soc. 1991, 113, 8016, incorporated herein by reference) was dissolved in acetone (100 mL): H2O (5 mL) and reacted with TsOH (140 mg, 0.74 mmol) at 45° C. for 5 h. After a standard aqueous work-up the material was purified by chromatography on SiO2 to give 4-(2-benzyloxy-ethyl)-cyclohexanone as a colorless oil (97%). After a standard aqueous work-up the material was purified by chromatography on SiO2
Source ID: ord-03e66e25526443aa881adc88ca3df186Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 8-(2-Benzyloxy-ethyl)-1,4-dioxa-spiro[4.5]decane (Intermediate K1, 1.02 g, 3.70 mmol) (prepared in accordance with the publication Ciufolini et. al. J. Amer. Chem. Soc. 1991, 113, 8016, incorporated herein by reference) was dissolved in acetone (100 mL): H2O (5 mL) and reacted with TsOH (140 mg, 0.74 mmol) at 45° C. for 5 h. After a standard aqueous work-up the material was purified by chromatography on SiO2 to give 4-(2-benzyloxy-ethyl)-cyclohexanone as a colorless oil (97%). After a standard aqueous work-up the material was purified by chromatography on SiO2
Source ID: ord-03e66e25526443aa881adc88ca3df186PubChem References
These sources are listed in the compound's public database record.
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