Acetone → HCID 19813064, compound

Participants

Reaction Steps

To a suspension of 4-methoxy-3-thiophenylacetic acid (1.61 g, 81 mmol) in acetone was added potassium carbonate (56 g, 400 mmol, 5 equivalents), followed by methyl iodide (11.5 g, 81 mmol, 1 equivalent). After stirring at ambient temperature for 5.5 hours, 2N aqueous hydrochloric acid solution (400 mL) was slowly added. The resulting solution was then extracted with 2×200 mL of THF/diethyl ether (1:1) followed by diethyl ether (400 mL). The combined organic layers were washed with 2×250 mL of 10% aqueous sodium thiosulfate and 250 mL of saturated aqueous sodium chloride solution (brine), dried over anhydrous magnesium sulfate, filtered and concentrated to give 56 g (96% yield) of the title compound as a pale yellow solid; DCI MS M/Z: 230 (M+NH4)+ ; 1H NMR (CD3OD) δ 3.36 (s, 3H), 3.53 (s, 2H), 3.82 (s, 3H), 6.83 (d, 1H, J=8.7 Hz), 7.02 (dd, 1H, J=8.7, 2.7 Hz), 7.06 (d, 1H, J=2.7 Hz).

Provenance & Evidence