Trimethylsilyl cyanide → 2-Hydroxy-3-methoxy-3-(4-morpholinophenyl)propanenitrile

Participants

Reaction Steps

To a solution of 2-methoxy-2-(4-morpholinophenyl)acetaldehyde (1.27 g, ˜5.1 mmol) in Et2O (35 mL) under a drying tube was added trimethylsilyl cyanide (1 mL, 8 mmol) and ZnI2 (50 mg, 0.16 mmol). After stirring at room temperature for 15.5 hrs, saturated aqueous NaHCO3 was added and the mixture was stirred several hrs. The mixture was diluted with EtOAc and H2O and the layers were separated. The organic layers were washed with saturated aqueous NaHCO3, dried over Na2SO4 and concentrated in vacuo to give 2-hydroxy-3-methoxy-3-(4-morpholinophenyl)propanenitrile as an orange foam (1.26 g). The product was used without further purification.

Provenance & Evidence