Acetic Acid → 5-(5-benzyl-1H-1,2,4-triazol-3-yl)-3-methylthiophene-2-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of butyl 5-(5-benzyl-1H-1,2,4-triazol-3-yl)-3-methylthiophene-2-carboxylate (0.23 g, 0.64 mmol) and 1 N aqueous sodium hydroxide (3.8 mL, 3.8 mmol) in ethanol (7.6 mL) was stirred at reflux for 1 h. The reaction mixture was cooled to 0° C. and acidified with glacial acetic acid to pH 5-6, and diluted with water (25 mL). The aqueous layer was extracted with dichloromethane (2×50 mL). The combined organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to afford the title compound as a colorless solid (0.18 g, 96%): 1H NMR (300 MHz, DMSO-d6) δ 12.94 (br s, 1H), 7.45 (s, 1H), 7.37-7.20 (m, 6H), 4.12 (s, 2H), 2.47 (s, 3H); MS (ES+) m/z 300.21 (M+1).

Provenance & Evidence