Diethyl Ether → 1-Phenylcyclopentanecarbonitrile

Participants

Reaction Steps

To a suspension of sodium hydride (60%) (7.5 g, 187.79 mmol) in dimethyl sulfoxide (100 mL) was added dropwise a mixture of phenyl acetonitrile (10 g, 85.36 mmol) and 1,4-dibromobutane (18.43 g, 187.79 mmol) dissolved in dimethyl sulfoxide: ether (120 mL, 1:1) at 0° C. Stirring was continued for 30 min at same temperature and at room temperature for 3 h. After completion of the reaction, the reaction mixture was quenched with 1N HCl (10 mL) and water (100 mL) was added. This mixture was extracted with ethyl acetate (3×100 mL), and the organic part separated and washed with water (3×100 mL) and brine (100 mL). The organic part was dried over sodium sulfate and concentrated to get a crude product which was purified on a CombiFlash column (eluted at 3% ethyl acetate in hexane) to afford 1-phenyl-cyclopentanecarbonitrile (276) (11.5 g, 78.68%) as a colorless liquid.

Provenance & Evidence