反応 #674307

反応方程式

sodium borohydride

ethyl 4-(benzyloxy)-1-cyanocyclohexanecarboxylate

H2O

→

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

収率 116.9%

溶媒

THF H2O

THF

反応条件

後処理

1. 1
   濃縮It was concentrated
2. 2
   その他to give the white solid
3. 3
   抽出The aqueous phase was extracted with EtOAc (4×30 mL)
4. 4
   洗浄The combined organic solution was washed with brine (30 mL)
5. 5
   乾燥dried over anhydrous Na2SO4
6. 6
   濃縮concentrated

実験手順

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.

出典