Aluminum(III) Chloride → HCID 24880047, compound

Participants

Reaction Steps

A solution of 3-(3,4,5-trimethoxybenzoyl)-6-methoxy-7-isopropoxybenzofuran (23 mg, 0.058 mmol, co-distilled with toluene before use) in dry dichloromethane (1 mL) was treated with solid aluminum chloride (16 mg, 0.116 mmol). The reaction mixture was stirred for 20 minutes at room temperature (monitored by tic) then quenched with saturated ammonium chloride solution and extracted with ethyl acetate (10 mL). The organic layer was washed with water (5 mL), dried over magnesium sulfate and concentrated under vacuum. The crude product was purified by flash chromatography (silica gel, eluent=hexane/diethyl ether/ethyl acetate; 80:19:1) to afford the title compound as a creamy white crystalline solid (18 mg, 86%); 1H NMR (300 MHz, CDCl3) δ 8.04(s, 1H, C2H), 7.63(d, 1H, J=8.53 Hz), 7.14(s, 2H, benzoyl Hs), 7.02(d, 1H, J=8.38 Hz), 3.97(s, 3H, OMe), 3.93(s, 3H, OMe), 3.89(s, 6H, 2×OMe); 13C NMR (75 MHz, CDCl3) δ 188.73(CO), 152.82, 151.24, 144.54, 143.30, 141.76, 133.97, 130.87, 120.92, 120.62, 112.43, 109.16, 106.06, 60.62, 56.85, 55.97.

Provenance & Evidence