Acetonitrile → Pentanenitrile, 4,4-dimethyl-3-oxo-

Participants

Reaction Steps

A suspension of 9.6 g of sodium hydride in 300 ml of tetrahydrofuran was stirred at 60° while a mixture of 23.2 g of methyl trimethylacetate and 8.2 g of acetonitrile was added in one portion. The reaction mixture was heated at reflux for five hours, and then cooled to room temperature and concentrated by evaporation of the solvent under reduced pressure. The product thus formed was dissolved in water and washed with dichloromethane. The aqueous layer was made acidic with 1N hydrochloric acid, and the acidic solution was extracted with fresh dichloromethane. The organic extracts were combined, washed with water, dried, and the solvent was removed by evaporation to give 14.0 g of cyanomethyl tert.-butyl ketone.

Provenance & Evidence