1,1,1-Trifluoro-2-propanol → 5-Cyano-6-(2,2,2-trifluoro-1-methylethoxy)nicotinic acid

Participants

Reaction Steps

To a solution of 363 mg (1.32 mmol) of methyl 5-cyano-6-(2,2,2-trifluoro-1-methylethoxy)nicotinate (from Step C) and 5.0 mL of 1,1,1-trifluoro-2-propanol in 5.0 mL of Et2O was added 530 μL (2.65 mmol) of 5.0 N NaOH. After stirring at rt overnight, the mixture was diluted with Et2O (20 mL), washed with diluted HCl (2×10 mL), dried over Na2SO4, and concentrated to give 327 mg of the title compound: 1H NMR (500 MHz, CD3OD) δ 1.46 (d, J=6.4, 3H), 5.92 (m, 1H), 8.52 (d, J=2.1, 1H), 8.86 (d, J=2.0, 1H).

Provenance & Evidence