Potassium Carbonate → 4,4-Dimethyl-2-(4-pyridinylmethyl)-3-isoxazolidinone

Participants

Reaction Steps

A mixture of 4-picolyl chloride hydrochloride (1.4 g, 0.0084 mol), 4,4-dimethyl-3-isoxazolidinone (1.0 g, 0.0084 mol), potassium carbonate (3.6 g, 0.0261 mol), and 18-Crown-6 (0.10 g, 0.0004 mol) in acetonitrile (50 mL) is stirred at room temperature overnight. The reaction mixture is poured into ethyl acetate (50 mL) and the mixture washed with water (3×30 mL). The organic layer is dried (magnesium sulfate) and concentrated under reduced pressure to yield an oil. This oil is passed through a silica gel pad eluting with 4:1 chloroform:methanol. The filtrate is concentrated and converted to 1.4 g of the maleate salt of the title compound.

Provenance & Evidence