반응 #487558

반응 방정식

4,4-dimethyl-1,3-cyclohexanedione

4′-chloro-4-ethylbiphen-3-yllead triacetate

dimethylaminopyridine

chloroform

→

2-(4′-chloro-4-ethylbiphen-3-yl)-4,4-dimethyl-1,3-cyclohexanedione

용매

toluene

dichloromethane

hydrochloric acid

반응 조건

후처리

1. 1
   온도cooled to room temperature
2. 2
   여과filtered through diatomaceous earth
3. 3
   기타The filtrate is partitioned
4. 4
   추출the aqueous layer is extracted with dichloromethane (50 ml)
5. 5
   세척washed with 2M aqueous hydrochloric acid (50 ml), brine (50 ml)
6. 6
   건조dried over anhydrous magnesium sulfate
7. 7
   여과filtered
8. 8
   기타the filtrate is evaporated under reduced pressure
9. 9
   기타The crude product is purified by preparative reverse phase HPLC

실험 절차

To a mixture of 4,4-dimethyl-1,3-cyclohexanedione (0.21 g, 1.5 mmol), 4′-chloro-4-ethylbiphen-3-yllead triacetate (1.0 g, 1.7 mmol) and dimethylaminopyridine (0.93 g, 7.6 mmol) is added anhydrous chloroform (11 ml) and anhydrous toluene (2.8 ml). The reaction mixture is heated at 80° C. for 4 hours and then cooled to room temperature. The mixture is diluted with dichloromethane (50 ml) and 2M aqueous hydrochloric acid (50 ml) and filtered through diatomaceous earth. The filtrate is partitioned, the aqueous layer is extracted with dichloromethane (50 ml) and the organic extracts are combined, washed with 2M aqueous hydrochloric acid (50 ml), brine (50 ml), dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure. The crude product is purified by preparative reverse phase HPLC to give 2-(4′-chloro-4-ethylbiphen-3-yl)-4,4-dimethyl-1,3-cyclohexanedione.

출처