Water → ethyl 2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-(tetrahydro-2H-pyran-4-yl)acrylate

Participants

Reaction Conditions

Reaction Steps

Ethyl 2-[3-bromo-4-(cyclopropylsulfonyl)phenyl]-3-(tetrahydro-2H-pyran-4-yl)acrylate (4.72 g), cyclopropylboronic acid (1.37 g), and tetrakis(triphenylphosphine)palladium (615 mg) were dissolved in toluene (142 mL), and to this solution were added tripotassium phosphate (4.07 g, 19.2 mmol) and water (7.1 mL). The mixture was stirred at 100° C. for 20 hours. It was cooled to room temperature, and water and ethyl acetate were added thereto. The organic layer was separated, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and then dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the obtained residue was purified by silica gel column chromatography to obtain ethyl 2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-(tetrahydro-2H-pyran-4-yl)acrylate (3.50 g) as an (E)/(Z)-mixture of olefin.

Provenance & Evidence