2-Cyclohexen-1-one → 3-Benzylcyclohexanone
反応式
[CH2:1]([Mg]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10]1(=[O:16])[CH2:15][CH2:14][CH2:13][CH:12]=[CH:11]1.[NH4+].[Cl-]>C1COCC1>[CH2:1]([CH:12]1[CH2:13][CH2:14][CH2:15][C:10](=[O:16])[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1参加物
5
反応条件
- 温度
- 0 °C
実験手順
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.