Sodium Carbonate → 4-[3-[6-(3-Benzo[1,3]dioxol-5-yl-5-methanesulfonyl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of 4-{2-(2-ethoxycarbonyl-ethyl)-3-[6-(3-iodo-5-methanesulfonyl-phenoxy)-hexyl]-phenoxy}-butyric acid ethyl ester (1.14 g, 1.65 mmol) in dimethoxyethane (15 mL) was stirred for 5 minutes at room temperature under nitrogen atmosphere. Then, tetrakis(triphenylphosphine)palladium(0) (386 mg, 0.33 mmol) was added at room temperature and the resulting light yellow solution was heated to 80° C. and stirred for 5 minutes. At this period, a solution of 3,4-(methylenedioxyphenyl)boronic acid (566 g, 3.3 mmol) in ethanol (16 mL) was added followed by a solution of sodium carbonate (351 mg, 3.3 mmol) in water (1.0 mL). The resulting light yellow suspension was stirred for 15 h at reflux. Then, the reaction mixture was cooled to room temperature and diluted with water (50 mL) and ethyl acetate (50 mL). The two layers were separated and the aqueous layer was extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with water (100 mL) and brine solution (100 mL). The organic layer was dried over anhydrous magnesium sulfate and filtration of the drying agent and removal of the solvent under reduced pressure gave the colored residue which was purified by using an ISCO 80 g column, eluting with 0-20% ethyl acetate in hexanes to afford 4-[3-[6-(3-benzo[1,3]dioxol-5-yl-5-methanesulfonyl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (972 mg, 86%) as a light brown viscous oil: ES(+)-HRMS m/e calcd for C37H46O10S (M+Na)+ 705.2704, found 705.2703.

Provenance & Evidence