Reaction #56615

Reaction equation

(5R)-1-allyl-5-[4′-(trifluoromethoxy)-1,1′-biphenyl-4-yl]-2-pyrrolidinone

p-toluenesulphonic acid hydrate

THF

H2O

→

(5R)-5-[4′-(Trifluoromethoxy)-1,1′-biphenyl-4-yl]-2-pyrrolidinone

Solvents

NaHCO3

ethyl acetate

Conditions

Workup

1. 1
   workup.ADDITIONare added
2. 2
   TemperatureThe yellow suspension is heated
3. 3
   Temperatureunder reflux for 3 h
4. 4
   Filtrationfiltered through kieselguhr
5. 5
   DryingThe combined organic phases are dried (Na2SO4)
6. 6
   Concentrationconcentrated under reduced pressure

Procedure

Under argon, (5R)-1-allyl-5-[4′-(trifluoromethoxy)-1,1′-biphenyl-4-yl]-2-pyrrolidinone (XVII-1) (0.41 g, 1.14 mmol) is initially charged in a Schlenk tube together with Pd[PPh3]4 (131.7 mg, 0.114 mmol) and p-toluenesulphonic acid hydrate (0.52 g, 2.74 mmol), and THF (2 ml, degassed) and 1 ml of H2O are added. The yellow suspension is heated under reflux for 3 h. For work-up, the mixture, which was cooled to room temperature, is diluted with NaHCO3 solution and admixed with ethyl acetate and filtered through kieselguhr. The combined organic phases are dried (Na2SO4) and concentrated under reduced pressure.

Source