Acetic Acid → 4-Cyclopropyl-5-phenylisoxazole-3-carboxylic acid

Participants

Reaction Steps

A solution of methyl 4-cyclopropyl-5-phenylisoxazole-3-carboxylate (170 mg, 0.699 mmol) and 1N aqueous sodium hydroxide (1 mL, 1.05 mmol) in methanol (6 mL) was heated to 80° C. in a sealed tube for 1 hr. The reaction mixture was acidified with acetic acid until the pH was ˜4. The mixture was concentrated, and the residue was purified by preparative HPLC to give 4-cyclopropyl-5-phenylisoxazole-3-carboxylic acid (124 mg). The compound had an HPLC ret. time=2.81 min.−Column. YMC S5 COMBISCREEN® 4.6×50 mm; Gradient time: 4 min; Flow rate=4 ml/min; Solvent A=10% MeOH−90% Water−0.2% H3PO4; Solvent B=90%

Provenance & Evidence