Reaction #487558

Reaction equation

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

Solvents

toluene

dichloromethane

hydrochloric acid

Conditions

Workup

1. 1
   Temperaturecooled to room temperature
2. 2
   Filtrationfiltered through diatomaceous earth
3. 3
   OtherThe filtrate is partitioned
4. 4
   Extractionthe aqueous layer is extracted with dichloromethane (50 ml)
5. 5
   Washwashed with 2M aqueous hydrochloric acid (50 ml), brine (50 ml)
6. 6
   Dryingdried over anhydrous magnesium sulfate
7. 7
   Filtrationfiltered
8. 8
   Otherthe filtrate is evaporated under reduced pressure
9. 9
   OtherThe crude product is purified by preparative reverse phase HPLC

Procedure

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.

Source