Sodium hydride → 3-(4-Cyanophenyl)tetrahydrofuran-3-carbonitrile

Participants

Reaction Steps

To a suspension of NaH (60% by weight, 1.2 g, 30 mmol) in 1-methylpyrrolidin-2-one (20 mL) was added a solution of 4-(cyanomethyl)benzonitrile (1.42 g, 10 mmol) and 1-chloro-2-(chloromethoxy)ethane (1.29 g, 10 mmol) in THF (10 mL) at −20° C. The mixture was allowed to warm to room temperature after completion of addition and stirred for 24 hours. The reaction was quenched by ice water and extracted with EtOAc (3×30 mL). The combined organic layers were washed with water (3×50 mL), brine (50 mL), dried over Na2SO4, filtered and concentrated to afford the crude product which was purified by Prep-TLC (EtOAc/hexane=1:5) to provide the title compound as a yellow oil (345 mg, 17.4%). LC-MS: m/z 172 (M−CN).

Provenance & Evidence