Triphenylphosphine → 3-(5-Methyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-isothiazole-5-carboxylic acid methyl ester

Participants

Reaction Steps

To a solution of (5-methyl-3-pyridin-2-yl-isoxazol-4-yl)-methanol (360 mg, 1.9 mmol) in THF (10 mL) was added 3-hydroxy-isothiazole-5-carboxylic acid methyl ester (300 mg, 1.9 mmol) and triphenylphosphine (594 mg, 1.9 mmol) at 0° C. under an argon atmosphere. Then diethyl azodicarboxylate (˜40% in toluene, 0.95 mL, 1.9 mmol) was added and the reaction mixture was stirred overnight at room temperature. Concentration and purification by chromatography (silica, heptane:ethyl acetate=4:1 to 1:4) afforded the title compound (350 mg, 56%) as a white solid. MS: m/e=332.2 [M+H]+.

Provenance & Evidence