Dimethylformamide → 4-{2-(2-Ethoxycarbonyl-ethyl)-3-[6-(3-iodo-5-methanesulfonyl-phenoxy)-hexyl]-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 (1.17 g, 2.49 mmol), 3-iodo-5-methanesulfonyl-phenol (620 mg, 2.08 mmol), and potassium carbonate (575 mg, 4.16 mmol) were added dimethylformamide (13.4 mL) and acetone (26.8 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 (100 mL). The organic compound was extracted into ethyl acetate (3×50 mL) and the combined organic extracts were washed with water (100 mL) and brine solution (100 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 40 g column, eluting with 2-20% ethyl acetate in hexanes to afford 4-{2-(2-ethoxycarbonyl-ethyl)-3-[6-(3-iodo-5-methanesulfonyl-phenoxy)-hexyl]-phenoxy}-butyric acid ethyl ester (1.3 g, 91%) as a colorless oil: ES(+)-HRMS m/e calcd for C30H41IO8S (M+Na)+ 711.1459, found 711.1460.

Provenance & Evidence