1,2-Dimethoxyethane → HCID 59496831, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-[3-[6-(3-bromo-5-ethoxy-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (305 mg, 0.5 mmol), phenylboronic acid (125 mg, 1.0 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (55 mg, 0.075 mmol), and cesium carbonate (331 mg, 1.0 mmol) in a microwave tube was added dimethoxyethane (5.9 mL) under nitrogen atmosphere at room temperature. The resulting brown reaction mixture was heated to 120° C. in a microwave for 30 minutes. The reaction mixture was diluted with ethyl acetate (50 mL) and the undissolved residue was filtered off and washed with water (50 mL). Then, the two layers of filtrate were separated and the aqueous layer was extracted with ethyl acetate (20 mL). The combined organic extracts were washed with water (50 mL) and brine solution (50 mL). The organic layer was dried over anhydrous magnesium sulfate and filtration of the drying agent and removal of the solvent under vacuum gave the colored residue which was purified by using an ISCO 40 column, eluting with 2-25% ethyl acetate in hexanes to obtain 4-[3-[6-(5-ethoxy-biphenyl-3-yloxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (255 mg, 84%) as a colorless viscous oil: ES(+)-LRMS m/e calcd for C37H48O7 (M+Na)+ 627.3292. found 627.3292.

Provenance & Evidence