Реакция #674307

Уравнение реакции

sodium borohydride

ethyl 4-(benzyloxy)-1-cyanocyclohexanecarboxylate

H2O

→

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

Выход 116.9%

Растворители

THF H2O

THF

Условия реакции

Обработка

1. 1
   КонцентрированиеIt was concentrated
2. 2
   Другоеto give the white solid
3. 3
   ЭкстракцияThe aqueous phase was extracted with EtOAc (4×30 mL)
4. 4
   ПромывкаThe combined organic solution was washed with brine (30 mL)
5. 5
   Сушкаdried over anhydrous Na2SO4
6. 6
   Концентрированиеconcentrated

Методика

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.

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