Potassium Hydroxide → 4-Ethynyl-5-methyl-3-phenyl-isoxazole

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-methyl-4-(5-methyl-3-phenyl-isoxazol-4-yl)-but-3-yn-2-ol (3.77 g, 15.6 mmol) in toluene (38 mL) was added potassium hydroxide (350 mg, 6.24 mmol) and the reaction mixture was stirred for 1.25 h at 110° C. before being cooled to ambient temperature and separated between ethyl acetate (500 mL) and aqueous ammonium chloride (1 M, 400 mL). The aqueous layer was extracted with ethyl acetate (500 mL) and the combined organic layers were dried over sodium sulfate and concentrated. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 90:10) afforded the title compound (2.50 g, 87%) as a yellow solid. MS: m/e=184.1 [M+H]+.

Provenance & Evidence