Reaction #674307

Reaction equation

sodium borohydride

ethyl 4-(benzyloxy)-1-cyanocyclohexanecarboxylate

H2O

→

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

Yield 116.9%

Solvents

THF H2O

THF

Conditions

Workup

1. 1
   ConcentrationIt was concentrated
2. 2
   Otherto give the white solid
3. 3
   ExtractionThe aqueous phase was extracted with EtOAc (4×30 mL)
4. 4
   WashThe combined organic solution was washed with brine (30 mL)
5. 5
   Dryingdried over anhydrous Na2SO4
6. 6
   Concentrationconcentrated

Procedure

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.

Source