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

Participants

Reaction Conditions

Reaction Steps

A solution of 4-{3-[6-(3-iodo-5-thiophen-3-yl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy}-butyric acid ethyl ester (2.13 g, 3.06 mmol) in dimethoxyethane (75 mL) was stirred for 5 minutes at room temperature under nitrogen atmosphere. Then, tetrakis(triphenylphosphine)palladium(0) (1.06 g, 0.92 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 benzo[1,3]dioxol-5-yl-boronic acid (1.53 g, 9.2 mmol) in ethanol (75 mL) was added followed by a solution of sodium carbonate (975 mg, 9.2 mmol) in water (6.0 mL). The resulting light yellow suspension was stirred for 24 h at reflux. Then, the reaction mixture was cooled to room temperature and diluted with water (100 mL) and ethyl acetate (100 mL). The two layers were separated and the aqueous layer was extracted with ethyl acetate (2×100 mL) and the combined organic extracts were washed with water (300 mL) and brine solution (300 mL). The organic layer was dried over anhydrous magnesium sulfate and filtration of the drying agent and removal of the solvent in vacuo gave the colored residue which was purified by using an ISCO 120 column, eluting with 0-20% ethyl acetate in hexanes to afford 4-{3-[6-(3-benzo[1,3]dioxol-5-yl-5-thiophen-3-yl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy}-butyric acid ethyl ester (1.125 g, 53.5%) as a light brown viscous oil: ES(+)-HRMS m/e calculated for C40H46O8S (M+Na)+ 709.2805, found 709.2808.

Provenance & Evidence