Reaktion #68750

Reaktionsgleichung

Jones' reagent

5-(4′-chloro-4-ethylbiphen-3-yl)-4-hydroxycyclopent-2-enone

→

2-(4′-chloro-4-ethylbiphen-3-yl)cyclopent-4-ene-1,3-dione

Ausbeute 80.6%

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONis added dropwise over 30 minutes to
2. 2
   Sonstigethe cooling bath is removed
3. 3
   workup.STIRRINGthe mixture is stirred for 1 hour at room temperature
4. 4
   workup.ADDITIONIsopropanol (500 ml) is added to the yellow slurry
5. 5
   workup.STIRRINGthe mixture is stirred at room temperature for 2 hours
6. 6
   workup.ADDITIONThe mixture is diluted with ethyl acetate
7. 7
   Waschenwashed with brine
8. 8
   Trocknendried over anhydrous magnesium sulfate
9. 9
   Filtrationfiltered
10. 10
    Sonstigethe filtrate is evaporated under reduced pressure

Vorschrift

Jones' reagent (126 ml of 1.67 M solution, 210.4 mmol) prepared according to the procedure described above, is added dropwise over 30 minutes to a cooled (ice-bath) solution of 5-(4′-chloro-4-ethylbiphen-3-yl)-4-hydroxycyclopent-2-enone (59.84 g, 191.3 mmol) in acetone (615 ml). The mixture is stirred for 20 minutes, then the cooling bath is removed and the mixture is stirred for 1 hour at room temperature. Isopropanol (500 ml) is added to the yellow slurry and the mixture is stirred at room temperature for 2 hours. The mixture is diluted with ethyl acetate and washed with brine, dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure to give 2-(4′-chloro-4-ethylbiphen-3-yl)cyclopent-4-ene-1,3-dione (47.94 g) as a yellow solid.

Quelle