Ethanol → 3-(Benzyloxyiminomethyl)-2,4,5-trifluorobenzoic acid ethyl ester

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Reaction Conditions

Reaction Steps

3-(Benzyloxyiminomethyl)-2,4,5-trifluorobenzoic acid (0.117 g, 0.378 mmol), 4-dimethylaminopyridine (0.023 g, 0.189 mmol), anhydrous ethanol (0.030 mL, 0.517 mmol) are mixed in dichloromethane (6 mL), cooled to 0° C., and treated with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.082 g, 0.427 mmol). After 2 hours at 0° C. and room temperature for 21 hours, the solvents are evaporated. The residue is dissolved in chloroform, washed with saturated NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification by chromatography (1:8 ethyl acetate/hexanes) provided the title compound (0.068 g). 1H NMR (200 MHz, CDCl3): δ 8.27 (s, 1H), 7.87–7.66 (m, 1H), 7.49–7.28 (m, 5H), 5.27 (s, 2H), 4.48–4.29 (q, 2H), 1.46–1.31 (t, 3H).

Provenance & Evidence