Iodine → HCID 67126114, compound

Participants

Reaction Steps

To a solution of 4-(4-chlorophenyl)-2-methyl-1-phenylbut-3-yn-2-ol (3D) (1.77 g, 6.53 mmol) in acetonitrile (50 mL) was added sodium bicarbonate (1.097 g, 13.06 mmol), followed by iodine (4.974 g, 19.60 mmol). The reaction mixture was stirred for 1.5 h, then diluted with diethyl ether. The organic layer was washed with 1 M sodium thiosulfate solution (50 mL). The aqueous layer was back-extracted with diethyl ether and the combined organic layer was dried (MgSO4), filtered, concentrated, adsorbed onto silica gel and purified by flash column chromatography (silica gel, hexanes) to give 3E as an off-white solid (1.8733 g). 1H-NMR: 300 MHz, (CDCl3) δ 7.74 (d, J=6.6 Hz, 1H), 7.73 (s, 1H), 7.48-7.40 (m, 3H), 7.24-7.20 (m, 2H), 7.13 (d, J=8.1 Hz, 2H), 2.64 (s, 3 H).

Provenance & Evidence