Réaction #674307

Équation de réaction

sodium borohydride

ethyl 4-(benzyloxy)-1-cyanocyclohexanecarboxylate

H2O

→

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

Rendement 116.9%

Solvants

THF H2O

THF

Conditions de réaction

Traitement

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

Mode opératoire

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