Water → (R)-1-(1-chloro-3-methylnaphthalen-2-yl)ethane-1,2-diol

Participants

Reaction Conditions

Reaction Steps

A biphasic mixture of AD-mix-β (45.7 g, excess) in tert-butanol (147 mL)/H2O (147 mL) was cooled to 0° C. and 1-chloro-3-methyl-2-vinyl-naphthalene (4.46 g, 22.0 mmol) was added. The reaction mixture was stirred for 7 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-(1-chloro-3-methylnaphthalen-2-yl)ethane-1,2-diol. 1H-NMR: 400 MHz, (CDCl3) δ 8.27 (d, J=8.4 Hz, 1H), 7.73 (d, J=7.6 Hz, 1H), 7.57-7.50 (m, 3H), 5.70 (dd, J=10.0, 4.0 Hz, 1H), 4.11 (t, J=10.4 Hz, 1H), 3.79 (dd, J=11.6, 4.0 Hz, 1H), 2.66 (s, 3H).

Provenance & Evidence