Ethyl isobutyrate → HCID 43157030, compound

Participants

Reaction Steps

To a mixture of [3,4-bis(methyloxy)phenyl]acetonitrile (2.0 g, 11 mmol) and ethyl 2-methylpropanoate (1.9 mL, 14 mmol) in ethanol (4 mL) was added a sodium ethoxide solution (21%, 8.4 mL, 23 mmol), and the resulting mixture was heated at reflux for 18 hours. After cooling to room temperature, it was poured into a mixture of ice-water (50 mL). This aqueous mixture was washed with dichloromethane (3×20 mL) then acidified to pH 1. The acidified mixture was extracted with ethyl acetate (3×30 mL). The combined extract was washed with aqueous sodium bicarbonate solution, brine, dried over sodium sulfate, filtered and concentrated to give 2-[3,4-bis(methyloxy)phenyl]-4-methyl-3-oxopentanenitrile as a brown oil (0.7 g, 3.4 mmol, 28% yield), MS (EI) for C14H17NO3: 248 (MH+).

Provenance & Evidence