tert-Butanol → HCID 67126996, compound

Participants

Reaction Conditions

Reaction Steps

A biphasic mixture of AD-mix-α (4.928 g) in tert-butanol (17.5 mL)/H2O (17.5 mL) was cooled to 0° C. and 1-(4-chlorophenyl)-3-methyl-2-vinyl-naphthalene (3F) (0.980 g, 3.52 mmol) was added. The reaction mixture was stirred for 6 h at 0° C., then stored at −20° C. overnight. The reaction was resumed for 10 h at 0° C., then stored at −20° C. overnight. The reaction was resumed for 8 h at 0° C. until complete. Sodium sulfite (5.3 g) was added at 0° C., then warmed to room temperature and stirred for 30 min to give a white mixture. The mixture was diluted with dichloromethane and H2O. The mixture was extracted with dichloromethane (3×) and the combined organic layer was dried (MgSO4), filtered, concentrated and purified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes) to give 3G as a white solid (0.9813 g). 1H-NMR: 300 MHz, (CDCl3) δ 7.72 (d, J=8.1 Hz, 1H), 7.65 (s, 1H), 7.50-7.303 (m, 3H), 7.26-7.07 (m, 4H), 4.92 (dd, J=9.9, 3.6 Hz, 1H), 3.94 (dd, J=10.2, 10.2 Hz, 1H), 3.57 (dd, J=11.1, 3.6 Hz, 1H), 2.69 (s, 3 H).

Provenance & Evidence