Lithium iodide → 4-{[5-(4-isopropylphenyl)-2-oxo-1,3,4-oxadiazol-3(2H)-yl]methyl}benzoic acid

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Reaction Steps

Methyl 4-{[5-(4-isopropylphenyl)-2-oxo-1,3,4-oxadiazol-3(2H)-yl]methyl}benzoate (50 mg, 0.14 mmol) is refluxed with lithium iodide (0.19 g, 1.4 mmol) in pyridine (5 mL) for 48 h and the mixture is diluted with water (30 mL) after cooling to room temperature. The precipitate is collected by filtration, washed with dichloromethane and dried in the air to furnish the desired product 4-{[5-(4-isopropylphenyl)-2-oxo-1,3,4-oxadiazol-3(2H)-yl]methyl}benzoic acid (31 mg, 66%), m.p. 217-219° C. 1H NMR (CDCl3, 300 MHz) δ (ppm) 1.13 (d, 6H) 2.70-2.90 (m, 1H), 4.86 (s, 2H), 7.17 (d, 2H), 7.30 (d, 2H), 7.59 (d, 2H), 7.89 (d, 2H). MS (ES+): m/e 339.

Provenance & Evidence