Potassium Carbonate → 4-{2-(2-Ethoxycarbonyl-ethyl)-3-[6-(3-iodo-5-methanesulfonyl-phenoxy)-hexyl]-phenoxy}-butyric Acid Ethyl Ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-[3-(6-bromo-hexyl)-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (3.79 g, 8.05 mmol), 3-iodo-5-methanesulfonyl-phenol (2.0 g, 6.71 mmol) in dimethylformamide (40 mL) and acetone (80 mL) was added potassium carbonate (9.25 g, 67.1 mmol). The resulting suspension was heated at 70° C. for 24 h. Then, the reaction mixture was cooled to room temperature, diluted with EtOAc and washed with 10% HCl and water. Then, the combined organic extracts were washed with brine. The organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product which was purified by using an ISCO 120 g column. The desired compound was eluted with 40% EtOAc-Hexanes. The desired fractions were combined and evaporated under reduced pressure to afford 4.5 g (97%) of title compound as a colorless oil. HR-ES(+) m/e calcd for C30H41O8SI (M+Na)+ 711.1459, found 711.1465.

Provenance & Evidence