Tetrahydrofuran → 1-Methyl-4-(pyridin-3-yl)azetidin-2-one

Participants

Reaction Steps

To a solution of 0.105 g (0.71 mmole) 4-(pyridin-3-yl)azetidin-2-one in 5 ml of dry tetrahydrofuran at stirring under argon atmosphere 0.113 g (2.83 mmole) 60% dispersion of sodium hydride in mineral oil was added. After the sparkling ceased at stirring and ice cooling 0.066 ml (0.150 g, 1.06 mmole) iodomethane was added and stirred for 2 hours. Carefully 10 ml of saturated aqueous ammonium chloride solution was added and stirred for 10 minutes. The reaction mixture was filtered and the aqueous solution was extracted with 5×10 ml of chloroform and the combined solutions were dried over magnesium sulfate and evaporated on rotavapor at 35° C. The residue (0.112 g) was purified by column chromatography on 10 g of silica gel with benzene-diethylamine 8-2 furnishing 0.0674 g (59%) pure product.

Provenance & Evidence