Triphenylphosphine → 5-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridine-2-carboxylic acid ethyl ester

Participants

Reaction Steps

To a solution of (5-methyl-3-phenyl-isoxazol-4-yl)-methanol (870 mg, 4.6 mmol) in THF (30 mL) was added 5-hydroxy-pyridine-2-carboxylic acid ethyl ester (999 mg, 6.0 mmol) and triphenylphosphine (1.57 g, 6.0 mmol) at ambient temperature under an argon atmosphere. Then diethyl azodicarboxylate (2.74 mL, 40% solution in toluene, 6.0 mmol) was added and the reaction mixture was stirred for 24 h at room temperature. The reaction mixture was evaporated and then diluted with water (40 mL) and extracted with ethyl acetate (3×50 mL). The combined organic layers were dried, filtered and concentrated in vacuo. Purification by chromatography (silica, heptane:ethyl acetate=100:0 to 2:3) afforded the title compound (481 mg, 31%) as a light yellow solid after trituration with dichloromethane. MS: m/e=339.3 [M+H]+.

Provenance & Evidence