3-Methoxybenzyl chloride → 1-(4-Iodophenyl)-3-(3-methoxyphenyl)-2-(4-methoxyphenyl)propan-1-one

Participants

Reaction Steps

Potassium bis(trimethylsilyl)amide (2.5 g, 12.5 mmol) was added to a solution of 1-(4-iodophenyl)-2-(4-methoxyphenyl)ethanone (4.225 g, 12.00 mmol) and THF (60 mL) at rt under N2. After 3.5 h, 3-methoxybenzyl chloride (2.2 mL, 15 mmol) was added. After 2.5 days, the reaction was quenched with saturated aqueous ammonium chloride solution (100 mL) and extracted with ethyl acetate (150 mL). The ethyl acetate extract was dried (MgSO4), filtered, concentrated, and purified by silica gel chromatography (99:1→4:1; hexanes:ethyl acetate) to give 4.7 g of 1-(4-iodophenyl)-3-(3-methoxyphenyl)-2-(4-methoxyphenyl)propan-1-one as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 7.83 (d, 2H), 7.76 (d, 2H), 7.20 (d, 2H), 7.09 (t, 1H), 6.81 (d, 2H), 6.76-6.65 (m, 3H), 5.13 (t, 1H), 3.67 (s, 3H), 3.66 (s, 3H), 3.35 (dd, 1H), 2.93 (dd, 1H).

Provenance & Evidence