反应详情

温度

20 °C

To a solution of trans-4-(methoxycarbonyl)cyclohexanecarboxylic acid (5.00 g, 26.9 mmol) in THF (30 mL) was added borane-dimethylsulfide complex (1.0 M in THF, 40 mL, 40 mmol) dropwise at 0° C. and then the mixture was stirred at 20° C. for 6 hours. Methanol (50 mL) was dropwise at 0° C., and then the reaction mixture was stirred at room temperature for 1 hour before being concentrated under reduced pressure. The residue was purified by chromatography on silica gel (ethyl acetate/petroleum ether) to give methyl trans-4-(hydroxymethyl)cyclohexanecarboxylate. MS ESI calc'd for C9H12O3 [M+H]+ 173. found 173. 1H NMR: (400 MHz, DMSO-d6) δ 4.39 (br s, 1H), 3.57 (s, 3H), 3.21-3.18 (m, 2H), 2.22-2.20 (m, 1H), 1.91-1.87 (m, 2H), 1.74-1.73 (m, 2H), 1.31-1.27 (m, 3H), 0.91-0.76 (m, 2H).

1. customwas dropwise at 0° C.
2. stirringthe reaction mixture was stirred at room temperature for 1 hour
3. concentrationbefore being concentrated under reduced pressure
4. customThe residue was purified by chromatography on silica gel (ethyl acetate/petroleum ether)