Water ethylacetate → HCID 86646253, compound

Participants

Reaction Steps

A mixture of 6-[3-phenyl-5-((E)-styryl)-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester (0.62 g, 1.5 mmol), osmium(VIII) oxide solution (0.38 mL of a 2.5% solution in tert-butanol, 0.037 mmol), sodium metaperiodate (1.29 g, 6 mmol), benzyltriethylammonium chloride (0.14 g, 0.6 mmol) in dioxane (13 mL) and water (4.5 mL) was irradiated in the microwave for 10 min at 120° C. Extractive workup (ethyl acetate/water) was followed by drying of the organic phase over sodium sulfate, filtered and concentrated. Purification by chromatography (silica, heptane:ethyl acetate=100:0 to 60:40) afforded the title compound as a light yellow solid (0.26 g, 51%). MS: m/e=339.3 [M+H]+.

Provenance & Evidence