Реакция #487558

Уравнение реакции

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

Растворители

toluene

dichloromethane

hydrochloric acid

Условия реакции

Обработка

1. 1
   Температураcooled to room temperature
2. 2
   Фильтрацияfiltered through diatomaceous earth
3. 3
   ДругоеThe filtrate is partitioned
4. 4
   Экстракцияthe aqueous layer is extracted with dichloromethane (50 ml)
5. 5
   Промывкаwashed with 2M aqueous hydrochloric acid (50 ml), brine (50 ml)
6. 6
   Сушкаdried over anhydrous magnesium sulfate
7. 7
   Фильтрацияfiltered
8. 8
   Другоеthe filtrate is evaporated under reduced pressure
9. 9
   ДругоеThe crude product is purified by preparative reverse phase HPLC

Методика

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.

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