Diphenylacetonitrile → Ethyl 5-cyano-5,5-diphenylpentanoate

Participants

Reaction Steps

To a stirring solution of diphenylacetonitrile (1-g) in tetrahydrofuran (10 ml) was added 60% sodium hydride (0.25 g) in small portions under ice-cooling. After completion of dropwise addition, the mixture was stirred for 20 minutes. Then, ethyl 4-bromobutyrate (0.94 ml) was added dropwise under ice-cooling and the mixture was further stirred at room temperature for 15 minutes. This reaction mixture was poured into ice-water and the organic layer that had separated out was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate, and concentrated to dryness. The group was purified by silica gel column chromatography to provide the title compound (0.87 g) as colorless oil.

Provenance & Evidence