Reaktion #1552042

Reaktionsgleichung

N-acetylphenylalanine 2-(phenylseleno)ethyl ester

H2O2

→

N-acetylphenylalanine vinyl ester

Lösungsmittel

CHCl3

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGAfter stirring the mixture for 12 hours at room temperature
2. 2
   Extraktionextracted with 3×50 ml of water
3. 3
   TrocknenThe organic phases were then dried over sodium sulfate
4. 4
   Sonstigethe solvent was removed
5. 5
   Temperaturwas refluxed for 24 hours
6. 6
   TemperaturAfter cooling
7. 7
   Sonstigethe solvent was removed
8. 8
   SonstigeFlash column—chromatography (PE:EE=3:1) yielded 1.3 g (84% of th., 93% of lit.) of a light-yellow liquid

Vorschrift

To a solution of 2.6 g (6.66 mmol) of N-acetylphenylalanine 2-(phenylseleno)ethyl ester in 20 ml of THF, 8 ml of a 30% H2O2 solution were added dropwise within 10 minutes at 0° C., and the solution was stirred at 0° C. for another 30 minutes. After stirring the mixture for 12 hours at room temperature, it was diluted with 80 ml of CHCl3 and extracted with 3×50 ml of water. The organic phases were then dried over sodium sulfate, and the solvent was removed. The residue was taken up in 70 ml of chloroform and was refluxed for 24 hours. After cooling, the solvent was removed. Flash column—chromatography (PE:EE=3:1) yielded 1.3 g (84% of th., 93% of lit.) of a light-yellow liquid.

Quelle