Sodium Cyanide → (1-Phenylcyclopentyl)acetonitrile

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of methanesulfonic acid 1-phenyl-cyclopentylmethyl ester (10 g, 39.37 mmol) in DMSO (30 ml) were added KI (0.6 g, 3.9 mmol) and NaCN (2.89 g, 59.05 mmol). It was then stirred at 140° C. for 16 h. After completion of the reaction, it was diluted with water, extracted with EtOAc and the organic layer was washed with water and brine. It was then dried over Na2SO4, concentrated and purified by normal column chromatography (15% EtOAc in hexanes) to afford the title compound as a colorless liquid (2.5 g, 34%).

Provenance & Evidence