Dimethylformamide → 4-{3-[6-(3-Iodo-5-thiophen-3-yl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy}-butyric acid ethyl ester

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Reaction Steps

To a mixture of 4-[3-(6-bromo-hexyl)-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (2.99 g, 6.35 mmol), 3-iodo-5-thiophen-3-yl-phenol (1.92 g, 6.35 mmol), and potassium carbonate (1.75 g, 12.7 mmol) were added N,N-dimethylformamide (50 mL) and acetone (100 mL) at room temperature. The resulting suspension was heated to reflux for 2 days. Then, the reaction mixture was cooled to room temperature and diluted with water (200 mL). The organic compound was extracted into ethyl acetate (3×100 mL) and the combined organic extracts were washed with water (300 mL) and brine solution (200 mL). The organic layers were dried over anhydrous magnesium sulfate and filtration of the drying agent and concentration of the solvent gave the crude product which was purified by using an ISCO 80 g column, eluting with 0-20% ethyl acetate in hexanes to afford 4-{3-[6-(3-iodo-5-thiophen-3-yl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy}-butyric acid ethyl ester (4.39 g, 99%) as a colorless oil: ES(+)-HRMS m/e calculated for C33H41IO6S (M+Na)+ 715.1561, found 715.1561.

Provenance & Evidence