반응 #159480

반응 방정식

4′-Chloro-3-methylbiphen-4-yllead triacetate

chloroform

toluene

hydrochloric acid

→

3-(4′-chloro-3-methylbiphen-4-yl)bicyclo[3.2.1]octane-2,4-dione

반응 조건

후처리

1. 1
   기타the reaction mixture is flushed with nitrogen for 15 minutes at ambient temperature
2. 2
   온도The reaction mixture is cooled to room temperature
3. 3
   여과filtered through a plug of diatomaceous earth
4. 4
   기타the two phases separated
5. 5
   추출The aqueous phase is extracted with dichloromethane (2×5 ml)
6. 6
   세척washed with water
7. 7
   건조dried over anhydrous sodium sulfate
8. 8
   여과The mixture is filtered
9. 9
   기타the filtrate is evaporated under reduced pressure
10. 10
    기타The residue is purified by column chromatography on silica gel

실험 절차

Bicyclo[3.2.1]-2,4-dione (0.20 g, 1.44 mmol) and 4-dimethylaminopyridine (0.88 g, 7.21_mmol) are added to a mixture of chloroform (4 ml) and toluene (1 ml), and the reaction mixture is flushed with nitrogen for 15 minutes at ambient temperature. 4′-Chloro-3-methylbiphen-4-yllead triacetate (0.95 g, 1.6 mmol) is added in one portion and the reaction mixture is stirred and heated to 80° C. under an atmosphere of nitrogen for 1 hour. The reaction mixture is cooled to room temperature, acidified to pH 1 with 2N aqueous hydrochloric acid, filtered through a plug of diatomaceous earth and the two phases separated. The aqueous phase is extracted with dichloromethane (2×5 ml), the organic phases are combined, washed with water, and dried over anhydrous sodium sulfate. The mixture is filtered, and the filtrate is evaporated under reduced pressure. The residue is purified by column chromatography on silica gel to give 3-(4′-chloro-3-methylbiphen-4-yl)bicyclo[3.2.1]octane-2,4-dione.

출처