反应详情

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%).

1. temperatureat reflux under nitrogen for 2 hr
2. temperaturereflux
3. temperatureAfter cooling the reaction mixture
4. washwashed with saturated sodium bicarbonate (100 mL) and water (2×100 mL)
5. extractionThe organic extract
6. dry with materialwas dried over sodium sulfate
7. filtrationfiltered
8. customThe solvent was removed in a rotary evaporator
9. customthe crude product was purified by chromatography on silica (80 g) with 2% ethyl acetate in heptane (4 L)