Methyl iodide → 4-[3-[6-(3-Bromo-5-methoxymethyl-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 (1.25 g, 2.1 mmol) in DMF (25 mL) were added sodium hydride (211 mg, 5.26 mmol) and iodomethane (747 mg, 5.26 mmol) at room temperature. The resulting suspension was stirred for 15 h and then the excess sodium hydride was quenched by slow addition of water (5 mL). The mixture was diluted with 1.0N hydrochloric acid (50 mL) and the organic compound was extracted into ethyl acetate (2×50 mL). The combined extracts were washed with brine solution (100 mL) and dried over anhydrous magnesium sulfate. Filtration of the drying agent and removal of the solvent under vacuum afforded the crude residue which was purified by using an ISCO 40 g column, eluting with 0-30% ethyl acetate in hexanes to obtain 4-[3-[6-(3-bromo-5-methoxymethyl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (1.03 g, 81%) as a colorless viscous oil: EI(+)-HRMS m/e calcd for C31H43BrO7 (M+Na)+ 629.2084. found 629.2085.

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