Sodium hydride → HCID 66718199, compound

Participants

Reaction Steps

A stirred solution of [3-phenyl-5-((E)-styryl)-isoxazol-4-yl]-methanol (1.50 g, 5.4 mmol) in THF (50 mL) was cooled in an ice bath. Sodium hydride (0.28 g of a 55% dispersion in mineral oil, 6.4 mmol) was added and the mixture was stirred for 30 min whilst allowing to warm to room temperature. To the resulting suspension was added methyl 6-chloropyridine-3-carboxylate (0.93 g, 5.4 mmol). After stirring for 2 h the reaction mixture was quenched with aqueous saturated sodium bicarbonate solution (20 mL). Evaporation of the organic solvent was followed by extraction with ethyl acetate. The organic phase was dried over sodium sulfate, filtered, concentrated and purified by chromatography (silica, heptane:ethyl acetate=90:10 to 60:40) to afford the title compound as an off-white solid (0.78 g, 35%). MS: m/e=413.5 [M+H]+.

Provenance & Evidence