Reacción #487558

Ecuación de reacción

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

Disolventes

toluene

dichloromethane

hydrochloric acid

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled to room temperature
2. 2
   Filtraciónfiltered through diatomaceous earth
3. 3
   OtroThe filtrate is partitioned
4. 4
   Extracciónthe aqueous layer is extracted with dichloromethane (50 ml)
5. 5
   Lavadowashed with 2M aqueous hydrochloric acid (50 ml), brine (50 ml)
6. 6
   Secadodried over anhydrous magnesium sulfate
7. 7
   Filtraciónfiltered
8. 8
   Otrothe filtrate is evaporated under reduced pressure
9. 9
   OtroThe crude product is purified by preparative reverse phase HPLC

Procedimiento

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.

Fuente