Sodium Hydroxide → 4-(5-(3,5-Dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acid

Participants

Reaction Conditions

Reaction Steps

Into a 50-mL round-bottom flask, was placed methanol (5 mL), methyl 4-[5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylbenzoate (60 mg, 0.13 mmol, 1.00 equiv), 15% NaOH (2 mL). The resulting solution was stirred for 2 h at 60° C. in an oil bath. The reaction mixture was cooled. The resulting mixture was concentrated under vacuum. The pH value of the solution was adjusted to 3-4 with hydrogen chloride (3 mol/L). The resulting solution was extracted with 3×10 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 3×5 mL of Brine. The organic phase was dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 57 mg (98%) of 4-[5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylbenzoic acid as a white solid.

Provenance & Evidence