Reaction #1552042

Reaction equation

N-acetylphenylalanine 2-(phenylseleno)ethyl ester

H2O2

→

N-acetylphenylalanine vinyl ester

Solvents

CHCl3

THF

Conditions

Workup

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

Procedure

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.

Source