反応 #487558

反応方程式

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

溶媒

toluene

dichloromethane

hydrochloric acid

反応条件

後処理

1. 1
   温度cooled to room temperature
2. 2
   ろ過filtered through diatomaceous earth
3. 3
   その他The filtrate is partitioned
4. 4
   抽出the aqueous layer is extracted with dichloromethane (50 ml)
5. 5
   洗浄washed with 2M aqueous hydrochloric acid (50 ml), brine (50 ml)
6. 6
   乾燥dried over anhydrous magnesium sulfate
7. 7
   ろ過filtered
8. 8
   その他the filtrate is evaporated under reduced pressure
9. 9
   その他The crude product is purified by preparative reverse phase HPLC

実験手順

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.

出典