Reacción #1121718

ord-ebb2d69525ac483c93f0a1552252adff

Ecuación de reacción

CC(=O)c1ccccc1
acetophenone
CC(C)(C)c1ccc(C(=O)Cl)cc1
4-tert-butylbenzoyl chloride
C=C(OC(=O)c1ccc(C(C)(C)C)cc1)c1ccccc1
1-phenylvinyl 4-tert-butylbenzoate
Rendimiento 57.0%

Disolventes

Condiciones de reacción

Temperatura
100°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.WAITThe mixture was then left
  2. 2
    Temperaturato cool
  3. 3
    Extracciónextracted with dichloromethane
  4. 4
    SecadoThe organic phase was dried over magnesium sulfate
  5. 5
    Otrothe solvent was removed under reduced pressure
  6. 6
    OtroA 2.12 g sample was purified by flash chromatography (hexane:dichloromethane 3:1)

Procedimiento

A mixture of 4.16 g (21.62 mmol) of acetophenone trimethylsilylenol, 4.33 g (22.01 mmol) of 4-tert-butylbenzoyl chloride and 136 mg of mercuric chloride was heated at 100° C. for 2 h. The mixture was then left to cool, water was added over the reaction crude and extracted with dichloromethane. The organic phase was dried over magnesium sulfate and the solvent was removed under reduced pressure. A 2.12 g sample was purified by flash chromatography (hexane:dichloromethane 3:1) giving 1.17 g of 1-phenylvinyl 4-tert-butylbenzoate. Yield 57%.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08545816B2uspto-grants-2013_10