Reaktion #674307

Reaktionsgleichung

sodium borohydride

ethyl 4-(benzyloxy)-1-cyanocyclohexanecarboxylate

H2O

→

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

Ausbeute 116.9%

Lösungsmittel

THF H2O

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenIt was concentrated
2. 2
   Sonstigeto give the white solid
3. 3
   ExtraktionThe aqueous phase was extracted with EtOAc (4×30 mL)
4. 4
   WaschenThe combined organic solution was washed with brine (30 mL)
5. 5
   Trocknendried over anhydrous Na2SO4
6. 6
   Einengenconcentrated

Vorschrift

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.

Quelle