3-Cyanopyridine → HCID 11019400, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-cyanopyridine (26.0 g, 0.25 mole) in dry diethyl ether (200 ml) was added dropwise over the hour to the Grignard reagent prepared from 1-bromo-3-methyl butane (40.7 g, 0.27 mole) and magensium (6.8 g, 0.26 mole) in dry diethyl ether (50 ml) under nitrogen. The mixture was heated at 35°C. for eight hours, cooled to room temperature, and diluted with cold saturated aqueous ammonium chloride solution (200 ml) followed by concentrated hydrochloric acid (50 ml). The mixture was stirred for five hours, the ether layer separated, and the aqeuous layer boiled for two hours. The aqueous layer was neutralised to pH9 with aqueous sodium hydroxide solution and extracted with diethyl ether (3×100 ml. The organic phase was dried (magnesium sulphate), concentrated under reduced pressure and distilled to give 3-methylbutyl 3-pyridyl ketone.

Provenance & Evidence