Lithium Hydroxide → (S)-4-(3-fluorophenyl)-7-({4-[1-hydroxy-1-(trifluoromethyl)propyl]-1H-1,2,3-triazol-1-yl}methyl)-2H-chromen-2-one

Participants

Reaction Steps

To a solution of (S)-1-(1-{[4-(3-fluorophenyl)-2-oxo-2H-chromen-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1-(trifluoromethyl)propyl 4-nitrobenzoate (15 mg, 0.025 mmol) in THF (2 mL), lithium hydroxide (0.125 mL of 1M solution, 0.125 mmol) was added. After 45 minutes stirring at room temperature, the reaction was quenched by the addition of 0.150 mL of a 2N HCl solution. The mixture was stirred 3 h at room temp and then heated 2 h at 40° C. After cooling, the reaction mixture was diluted with ethyl acetate, washed with brine, dried over MgSO4, filtered and concentrated. The crude residue obtained was purified by column chromatography to afford the title compound. 1H NMR (400 MHz, acetone-d6): 8.21 (s, 1H), 7.7-7.6 (m, 1H), 7.53 (d, 1H), 7.42-7.3 (m, 5H), 6.41 (s, 1H), 5.87 (s, 2H), 5.48 (s, 1H), 2.4-2.3 (m, 1H), 2.1-2.0 (m, 1H), 0.87 (t, 3H).

Provenance & Evidence