تفاعل #159463

معادلة التفاعل

hydrochloric acid

toluene

3,5-dimethylbiphen-4-yllead triacetate

bicyclo[3.2.1]octane-2,4-dione

→

3-(3,5-dimethylbiphen-4-yl)bicyclo[3.2.1]octane-2,4-dione

المذيبات

chloroform

ظروف التفاعل

المعالجة

1. 1
   workup.DISSOLUTIONis dissolved
2. 2
   درجة الحرارةthe mixture is heated
3. 3
   درجة الحرارةunder reflux for 1 hour
4. 4
   درجة الحرارةThe reaction mixture is cooled to room temperature
5. 5
   ترشيحfiltered
6. 6
   استخلاصthe filtrate is extracted with dichloromethane
7. 7
   تجفيفdried over anhydrous magnesium sulfate
8. 8
   ترشيحfiltered
9. 9
   أخرىthe filtrate evaporated in vacuo
10. 10
    أخرىThe residue is further purified by column chromatography on silica gel

الإجراء التجريبي

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.

المصدر