2-Cyclohexen-1-one → 3-Benzylcyclohexanone

Temperature

0 °C

To a solution of benzylmagnesiumchloride in THF (1.31 M, 393 mmol, 300 mL) CuCl (1.9 g) was added and the mixture was cooled to 0° C. The mixture was stirred for 6 min., and a solution of cyclohex-2-enone (193 mmol, 18.9 g) in THF (75 mL) was added dropwise at 0° C. over a period of 1 h. The reaction mixture was warmed to RT overnight. After cooling again to 0° C., saturated aqueous NH4Cl (450 mL) was added and the layers were separated. The aqueous layer was extracted with EtOAc (2×500 mL). The combined org. layers were washed with saturated aqueous NH4Cl (500 mL) and dried over Na2SO4. After evaporation, the crude product was subjected to column chromatography (SiO2, EtOAc/Hept=1/19→1/9) to give two fractions of product 01-1. Fraction 1 (23.5 g, 125 mmol, 65%, yellow oil) was used in the next step.

1. temperatureThe reaction mixture was warmed to RT overnight
2. temperatureAfter cooling again to 0° C.
3. customthe layers were separated
4. extractionThe aqueous layer was extracted with EtOAc (2×500 mL)
5. washlayers were washed with saturated aqueous NH4Cl (500 mL)
6. dry with materialdried over Na2SO4
7. customAfter evaporation

ORD record

ord-d7d5cb435440472fa34661e4b63a8ef2

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07524853B2