Sodium Cyanide → (3R)-3-(4-chlorophenyl)-3-cyclopropylpropanenitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of (2R)-2-(4-chlorophenyl)-2-cyclopropylethyl 4-methylbenzenesulfonate (11.00 g, 31.3 mmol) and NaCN (4.62 g, 94.3 mmol) in dimethyl sulfoxide (100 ml) is heated at to 90° C. for 3 hours. The dimethyl sulfoxide was removed in vacuo and the resulting mixture is partitioned between water (200 ml) and diethyl ether (200 ml). The organic layer is dried over anhydrous sodium sulfate and concentrated in vacuo. The residue chromatographed on silica gel eluting with ether:hexane (25:75) to afford the title compound as a colorless oil (5.62 g, 87%) which is characterized by 1HNMR, IR and mass spectral analyses.

Provenance & Evidence