반응 #71597

반응 방정식

hydrochloric acid

toluene

5-(tetrahydropyran-4-yl)cyclohexane-1,3-dione

3,5-dimethylbiphen-4-yllead triacetate

→

2-(3,5-dimethylbiphen-4-yl)-5-(tetrahydropyran-4-yl)cyclohexane-1,3-dione

용매

chloroform

chloroform

반응 조건

후처리

1. 1
   workup.DISSOLUTIONare dissolved
2. 2
   온도The reaction mixture is heated
3. 3
   온도under reflux for 1 hour
4. 4
   온도The reaction mixture is cooled to room temperature
5. 5
   여과filtered
6. 6
   추출the filtrate is extracted with dichloromethane (2×40 ml)
7. 7
   건조dried over anhydrous magnesium sulfate
8. 8
   여과filtered
9. 9
   기타the filtrate is evaporated in vacuo
10. 10
    기타The residue is purified by column chromatography on silica gel

실험 절차

To a mixture of 5-(tetrahydropyran-4-yl)cyclohexane-1,3-dione (196 mg; 1 mmol) and 4-dimethylaminopyridine (610 mg; 5 mmol) is added dry chloroform (4 ml) under an atmosphere of nitrogen, and the mixture is stirred at room temperature until all the solids are dissolved. To this solution is then added dry toluene (2 ml) and a solution of 3,5-dimethylbiphen-4-yllead triacetate (1.2 mmol) in chloroform. The reaction 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 (2×40 ml). The organic extracts are combined, dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated in vacuo. The residue is purified by column chromatography on silica gel to give 2-(3,5-dimethylbiphen-4-yl)-5-(tetrahydropyran-4-yl)cyclohexane-1,3-dione.

출처