反应详情

Under nitrogen stream, 4-bromophenylboric acid (15.7 g, 78 mmol), (R)-BINAP 1.17 g (1.9 mmol), and acetylacetonato bis(ethylene)rhodium(I) (486 mg, 1.9 mmol) were dissolved in a solvent mixture of 1,4-dioxane (150 mL) and water (15 mL), followed by degassing with ultrasonic waves. Subsequently, cyclopentenone (2.6 mL, 31 mmol) was added and the mixture was stirred under reflux with heating for 3 hours. The reaction solution was cooled to room temperature, followed by addition of saturated aqueous sodium bicarbonate solution, and then the solvent was distilled off under reduced pressure. The aqueous phase was extracted with ethyl acetate. The extracted solution was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue obtained was purified by column chromatography (ethyl acetate/hexane:20/80-30/70) to give the title compound (6.94 g, 91%).

1. customby degassing with ultrasonic waves
2. temperatureunder reflux
3. temperaturewith heating for 3 hours
4. distillationthe solvent was distilled off under reduced pressure
5. extractionThe aqueous phase was extracted with ethyl acetate
6. dry with materialThe extracted solution was dried over anhydrous magnesium sulfate
7. distillationthe solvent was distilled off under reduced pressure
8. customThe residue obtained
9. customwas purified by column chromatography (ethyl acetate/hexane:20/80-30/70)