Acetonitrile → 3-Cyclopentyl-3-oxopropanenitrile

Participants

Reaction Conditions

Reaction Steps

To a suspension of sodium hydride (1.87 g, 55% in mineral oil, 42.9 mmol) in THF (10 ml) was added a solution of methyl cyclopentanecarboxylate (5 g, 39.0 mmol) and acetonitrile (1.92 g, 2.45 ml, 46.8 mmol) in THF (3 ml) dropwise at 70° C. The mixture was heated to 70° C. overnight, then cooled to room temperature, diluted with 1N HCl and extracted with EtOAc. The combined organic layers were washed with water and brine, dried with Na2SO4 and evaporated. The remaining residue was purified by column chromatography (silica gel, heptane/EtOAc 95:5-85:15) to afford the title compound (4105 mg, 77%) as light yellow liquid.

Provenance & Evidence