تفاعل #487558

معادلة التفاعل

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

المذيبات

toluene

dichloromethane

hydrochloric acid

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooled to room temperature
2. 2
   ترشيحfiltered through diatomaceous earth
3. 3
   أخرىThe filtrate is partitioned
4. 4
   استخلاصthe aqueous layer is extracted with dichloromethane (50 ml)
5. 5
   غسيلwashed with 2M aqueous hydrochloric acid (50 ml), brine (50 ml)
6. 6
   تجفيفdried over anhydrous magnesium sulfate
7. 7
   ترشيحfiltered
8. 8
   أخرىthe filtrate is evaporated under reduced pressure
9. 9
   أخرىThe crude product is purified by preparative reverse phase HPLC

الإجراء التجريبي

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.

المصدر