Réaction #159439

Équation de réaction

5-chloro-2-methylphenyllead triacetate

bicyclo[3.2.1]octane-2,4-dione

toluene

→

3-(5-chloro-2-methylphenyl)bicyclo[3.2.1]octane-2,4-dione

Rendement 33.3%

Solvants

chloroform

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGthe mixture is stirred at 80° C. for 1 hour
2. 2
   Température(pre-heated oil bath)
3. 3
   Températureto cool to room temperature
4. 4
   Autrequenched with 1M hydrochloric acid
5. 5
   Autrethe organic phase separated
6. 6
   LavageThe aqueous phase is further washed with dichloromethane (×2)
7. 7
   Autreagain the phases are separated
8. 8
   AutreAll organics are combined then evaporated under reduced pressure
9. 9
   Autreto give a crude oil
10. 10
    AutrePurification by preparative reverse-phase HPLC

Mode opératoire

To a solution of 5-chloro-2-methylphenyllead triacetate (0.41 g, 0.80 mmol) in chloroform (4 ml) is added bicyclo[3.2.1]octane-2,4-dione (0.10 g, 0.72 mmol) and 4-dimethylaminopyridine (0.46 g, 3.62 mmol), and the reaction mixture is stirred at room temperature for 5 minutes. Next toluene (1 ml) is added, and the mixture is stirred at 80° C. for 1 hour (pre-heated oil bath). The reaction mixture is allowed to cool to room temperature, quenched with 1M hydrochloric acid, and the organic phase separated. The aqueous phase is further washed with dichloromethane (×2), and again the phases are separated. All organics are combined then evaporated under reduced pressure to give a crude oil. Purification by preparative reverse-phase HPLC furnishes 3-(5-chloro-2-methylphenyl)bicyclo[3.2.1]octane-2,4-dione (0.063 g, 33%) as a colourless gum.

Source