Reaktion #487558

Reaktionsgleichung

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

Lösungsmittel

toluene

dichloromethane

hydrochloric acid

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle