1,2-Dimethoxyethane → 1-(2'-(Benzyloxy)-3'-tert-butylbiphenyl-3-yl)ethanone

Participants

Reaction Steps

A mixture of crude 35 (3.88 g, 10 mmol), 3-acetylphenyl boronic acid (1.8 g, 11 mmol, 1.1 equiv.), bis(triphenylphosphine)palladium(II) dichloride (20 mg), glyme (5.5 mL) and sodium bicarbonate (2.7 g) in water (55 mL) was kept at reflux under nitrogen for 2 hr. Additional palladium catalyst (20 mg) was added and reflux continued for 3 hr. After cooling the reaction mixture was diluted with ethyl acetate (150 mL) and washed with saturated sodium bicarbonate (100 mL) and water (2×100 mL). The organic extract was dried over sodium sulfate and filtered. The solvent was removed in a rotary evaporator and the crude product was purified by chromatography on silica (80 g) with 2% ethyl acetate in heptane (4 L) to afford 36 (3.12 g, 87%).

Provenance & Evidence