酮还原成醇

产物官能团类型


硼氢化钠

反应机理

与将醛还原成醇的反应类似,反应优选在甲醇溶剂中,0 °C或者室温的反应条件即可

案例

To a solution of the SM (15.5 g, 71.3 mmol) in MeOH (150 mL) at 0 C was added NaBH4 (3.51 g, 93.7 mmol). The resulting mixture was stirred at 0 C for 2 h, after which time it was allowed to warm to RT. Sat aq NH4Cl (200 mL) was added and the mixture was extracted with EtOAc. The combined organics were washed with brine, dried (MgSO4), and concentrated. The resulting material was purified by silica gel column chromatography (eluting with 40-50% EtOAc/heptane) to provide product B as a pale yellow oil which solidified on standing to a white solid (3.81 g, 24%). The second eluting compound was product A, which was isolated as a white solid (10.57 g, 68%). [combined yield: 14.38 g, 92%]

Patent Reference: WO2012069948, page 82

反应机理