1,2-Dimethoxyethane → 1-1,2-Benzisoxazol-3-ylmethyl-3-isopropenyl-1,3-dihydro-benzimidazol-2-one

Participants

Reaction Conditions

Reaction Steps

A 25 ml pear-shaped flask was charged with sodium hydride (60% oil dispersion, 68 mg, 1.7 mmol) which was washed with hexanes and then diluted with DME (3 ml). The 1-{2-(2-fluoro-phenyl)-2-[hydroxyimino]-ethyl}-3-isopropenyl-1,3-dihydro-benzimidazol-2-one (0.5 g, 1.5 mmol) was introduced as a DME (3 ml) solution in a dropwise manner. The resulting mixture was warmed to 85° C. for 20 h and cooled to ambient temperature. The reaction was diluted with water and the product was extracted into ethyl acetate (2×). The combined organics were dried (MgSO4), filtered and concentrated to give the crude product which was purified via column chromatography (silica gel, 40% EtOAc/hexanes). The product-containing fractions were combined and concentrated to give 0.26 g (55%) of the desired product.

Provenance & Evidence