Reacción #674307

Ecuación de reacción

sodium borohydride

ethyl 4-(benzyloxy)-1-cyanocyclohexanecarboxylate

H2O

→

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

Rendimiento 116.9%

Disolventes

THF H2O

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónIt was concentrated
2. 2
   Otroto give the white solid
3. 3
   ExtracciónThe aqueous phase was extracted with EtOAc (4×30 mL)
4. 4
   LavadoThe combined organic solution was washed with brine (30 mL)
5. 5
   Secadodried over anhydrous Na2SO4
6. 6
   Concentraciónconcentrated

Procedimiento

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.

Fuente