Diethyl Ether → 1-Phenylcyclopentanecarbonitrile

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To a suspension of sodium hydride (60%, 18.8 g, 470.08 mmol) in dimethyl sulfoxide (125 mL) was added dropwise a mixture of phenyl acetonitrile (19-01) (25 g, 213.6 mmol) and 1,4-dibromo-butane (20) (25.5 mL, 213.67 mmol) dissolved in dimethyl sulfoxide:ether (300 mL, 1:1). The mixture was stirred at room temperature for 3 h. After completion of the reaction, it was quenched with 1N HCl. The mixture was extracted with ethyl acetate, the separated organic part was dried and concentrated to get a crude product which was purified using normal silica column using 3% ethyl acetate in hexane to of ford 1-phenyl-cyclopentanecarbonitrile (21-01) (34 g, 92.92%) as a yellow liquid.

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