Iodoethane → 4-[3-[6-(3-Bromo-5-ethoxymethyl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester

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Reaction Steps

To a solution of 4-[3-[6-(3-bromo-5-hydroxymethyl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (1.0 g, 1.68 mmol) in N,N-dimethylformamide (10 mL) was added iodoethane (403 μL, 5.04 mmol) and sodium hydride, 60% dispersion in mineral oil (202 mg. 5.04 mmol) at room temperature. The resulting suspension was stirred for 5 h. Then, the reaction mixture was diluted with water and brine. The organic compound was extracted into ethyl acetate and the combined organic extracts were washed with brine solution. The organic layers were dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The crude material was purified by column chromatography (Isco™ 40 g) with 0-30% ethyl acetate/hexanes as eluting solvents to afford the title compound (550 mg, 53%) as a colorless oil.

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