tert-Butanol → 6-(1,2-dihydroxy-ethyl)-3-(3-methyl-isoxazol-5-yl)-4-phenyl-1H-quinolin-2-one

Participants

Reaction Steps

AD-mix β was dissolved in 50% aq. tert-butanol (10 mL) followed by 3-(3-methyl-isoxazol-5-yl)-4-phenyl-6-vinyl-1H-quinolin-2-one (d) (60 mg, 0.18 mmol) and the resulting mixture was stirred at room temperature overnight. Sodium sulfite (0.3 g) was added and stirring was continued until the solution cleared. The mixture was extracted with ethyl acetate (1×20 mL, 2×10 mL) and the combined organic layers were dried (MgSO4), filtered, and concentrated. The residue was purified by flash chromatography on silica gel (5% methanol in DCM) to give 6-(1,2-dihydroxy-ethyl)-3-(3-methyl-isoxazol-5-yl)-4-phenyl-1H-quinolin-2-one (e) (66 mg, 100%). 1H NMR (300 MHz, DMSO-d6) δ 12.3 (s, 1H), 7.56 (dd, J=2.6, 6.9 Hz, 1H), 7.49-7.41 (m, 3H), 7.37 (d, J=8.6 Hz, 1H), 7.27-7.18 (m, 1H), 7.09-7.04 (m, 1H), 6.41 (s, 1H), 5.25-5.20 (m, 1H), 4.65 (dd, J=6.4, 7.7Hz, 1H), 4.46-4.36 (m, 1H), 2.12 (s, 3H). MS: 363.2 (M+H).

Provenance & Evidence