p-Anisoyl chloride → LY88074 Trimethyl ether

Participants

Reaction Conditions

Reaction Steps

2-(4-Methoxyphenyl-6-methoxybenzo[b]thiophene (10 g, (37 mmol) of was dissolved in 700 mL of 1,2-dichloroethane and the mixture cooled to 0° C. To the reaction solution was added, slowly, a mixture of 4-methoxybenzoyl chloride (6.31 g, 37 m mol) and aluminum chloride (5.07 g 38 mmol). The reaction was allowed to proceed at 0° C. for two hours and was terminated by pouring into ice-water. The organic layer was separated and aqueous layer extracted with chloroform. The organic layers were combined, washed with saturated aqueous sodium bicarbonate and water, dried over magnesium sulfate, and filtered. The volatiles were removed by evaporation yielding a yellow oil, which was dissolved in 500 mL of methanol and 15 mL of 5N sodium hydroxide and refluxed until the methanol had evaporated (thirty minutes). The resulting oil was dissolved in diethylether, washed with brine, and evaporated. This yielded 14.6 g of a yellow oil which was purified by chromatography. This yielded 13.9 g of the title compound as a yellow oil. EA calculated for C24H20O4S: C, 71.25; H, 4.98; O, 15.82; S, 7.93. Found: C, 71.25; H, 4.90; O, 15.78; S, 7.65. MS(EI): m/e=404 (M+).

Provenance & Evidence