Water → (R)-1-(5-bromo-7-methylquinolin-6-yl)ethane-1,2-diol

Participants

Reaction Conditions

Reaction Steps

A biphasic mixture of AD-mix-β (1.2 g, excess) in tert-butanol (4.5 mL)/H2O (4.5 mL) was cooled to 0° C. and 5-bromo-7-methyl-6-vinylquinoline (210 mg, 0.85 mmol) was added. The reaction mixture was stirred for 2 days at 0° C. The mixture was diluted with ethyl acetate, washed with water and brine, dried over Na2SO4, filtered and concentrated and purified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes) to give (R)-1-(5-bromo-7-methylquinolin-6-yl)ethane-1,2-diol. 1H-NMR: 400 MHz, (CD3OD) δ 8.82 (d, J=4.4 Hz, 1H), 8.76 (d, J=8.8 Hz, 1H), 7.84 (s, 1H), 7.61-7.57 (m, 1H), 5.84 (dd, J=8.8, 4.8 Hz, 1H), 4.00 (dd, J=11.2, 8.8 Hz, 1H), 3.80 (dd, J=11.2, 4.4 Hz, 1H), 2.81 (s, 3 H).

Provenance & Evidence