反应详情

To a mixture of bicyclo[3.2.1]octane-2,4-dione (0.553 g, 4 mmol) in dry chloroform (12 ml) is added 4-dimethylaminopyridine (2.44 g, 20 mmol), and the mixture is stirred at room temperature until all the solid is dissolved. To this solution is then added dry toluene (8 ml), and 3,5-dimethylbiphen-4-yllead triacetate (0.5 M solution in dry chloroform, 10 ml, 5 mmol), and the mixture is heated under reflux for 1 hour. The reaction mixture is cooled to room temperature, acidified to pH=1 with 2N aqueous hydrochloric acid, filtered and the filtrate is extracted with dichloromethane. The organic extracts are combined, dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated in vacuo. The residue is further purified by column chromatography on silica gel to give 3-(3,5-dimethylbiphen-4-yl)bicyclo[3.2.1]octane-2,4-dione as a white powder.

1. dissolutionis dissolved
2. temperaturethe mixture is heated
3. temperatureunder reflux for 1 hour
4. temperatureThe reaction mixture is cooled to room temperature
5. filtrationfiltered
6. extractionthe filtrate is extracted with dichloromethane
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationfiltered
9. customthe filtrate evaporated in vacuo
10. customThe residue is further purified by column chromatography on silica gel