Sodium Hydroxide → 4-[(E)-3-(imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenyl)benzoic acid

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A solution of methyl 4-[3-(imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenyl)benzoate (B and Z isomers) (1.9 g; 5.6 mmol) and 2N aqueous sodium hydroxide solution (8.5 ml; 17 mmol) in methanol (100 ml) was refluxed for 9 hours. After evaporation and acidification with 12N HCl (1.5 ml), the resulting solid was washed with distilled water and ether, taken up in dichloromethane/methanol (99/1) to give 4-[(E)-3-(imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenyl)benzoic acid (E isomer) after evaporation as a foam. Yield: 89%

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