Potassium Phosphate, Tribasic → Methyl(4-cyclopropylphenyl)acetate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl(4-iodophenyl)acetate (1.5 g, 5.4 mmol), cyclopropylboronic acid (607 mg, 7.06 mmol), potassium phosphate (4.04 g, 29.7 mmol) and tricyclohexylphosphine (152 mg, 10 mol %) in 25 mL toluene under nitrogen was added water (1.25 mL) and palladium acetate (61 mg, 5 mol %). The mixture was heated to 100° C. for 10 hours. After cooling to room temperature, water and ethyl acetate were added and the mixture was filtered through a Celite® pad to remove insoluble material. The layers were separated and the water layer was washed 2× with ethyl acetate. The combined organic layers were washed with brine and dried over anhydrous magnesium sulfate. Solvent removal gave 1.5 g of a dark yellow paste which was purified by silica chromatography on an ISCO (Teledyne Corp., Thousand Oaks, Calif.) column, eluting with a gradient 0/100 to 30/70 ethyl acetate/heptanes, to give methyl(4-cyclopropylphenyl)acetate as a yellow semi-solid (718 mg, 69%).

Provenance & Evidence