Acetonitrile → 3-(1-Methylcyclopropyl)-3-oxopropanenitrile

Participants

Reaction Steps

A mixture of 61.1 g of acetonitrile and 108.3 g of methyl 1-methylcyclopropanecarboxylate was added drop-by-drop over a one-hour period to a stirred, refluxing mixture of 35.8 g of sodium hydride and 650 ml of tetrahydrofuran. The resulting mixture was stirred and refluxed for a further 18 hours, then most of the solvent was evaporated in a rotary evaporator. The residue was dissolved in 1 liter of water, and the solution was acidified with hydrochloric acid and extracted with ether. The extract was dried (MgSO4) and concentrated. The residue, a liquid, was fractionally distilled to give (1-methylcyclopropylcarbonyl)acetonitrile (D) as a colorless oil which crystallized on standing, m.p.: 32°-33° C.

Provenance & Evidence