反应 #674307

反应方程式

sodium borohydride

ethyl 4-(benzyloxy)-1-cyanocyclohexanecarboxylate

H2O

→

4-(benzyloxy)-1-(hydroxymethyl)cyclohexanecarbonitrile

收率 116.9%

溶剂

THF H2O

THF

反应条件

后处理

1. 1
   浓缩It was concentrated
2. 2
   其他to give the white solid
3. 3
   萃取The aqueous phase was extracted with EtOAc (4×30 mL)
4. 4
   洗涤The combined organic solution was washed with brine (30 mL)
5. 5
   干燥dried over anhydrous Na2SO4
6. 6
   浓缩concentrated

实验过程

To a solution of sodium borohydride (186 mg, 4.92 mmol, 2.5 equiv) in THF/H2O (5/0.5 mL) was added a solution of ethyl 4-(benzyloxy)-1-cyanocyclohexanecarboxylate (565 mg, 1.97 mmol, 1.0 equiv) in THF (dry, 3 mL) dropwise. The reaction mixture was stirred at room temperature for 18 hrs. It was concentrated to give the white solid. H2O (20 mL) was added. The aqueous phase was extracted with EtOAc (4×30 mL). The combined organic solution was washed with brine (30 mL), dried over anhydrous Na2SO4 and then concentrated to give 565 mg of crude 4-(benzyloxy)-1-(hydroxymethyl)cyclohexanecarbonitrile as a colorless sticky oil which was not purified and submitted for the next reaction.

来源