Reacción #4082

ord-d91476894bba4ff4b3f1ab9b2aac825a

Ecuación de reacción

CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(=O)C=C[C@]4(C)[C@H]3CC[C@]12C
cholesta-1,4,6-trien-3-one
CS(=O)(=O)O
methanesulfonic acid
C=C(C)OC(C)=O
isopropenyl acetate
→
CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4CC(O)C=C[C@]4(C)[C@H]3CC[C@]12C
cholesta-1,5,7-trien-3-ol
Rendimiento 61.2%

Reactantes

CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C=CC4=CC(=O)C=C[C@]4(C)[C@H]3CC[C@]12C
cholesta-1,4,6-trien-3-one
CS(=O)(=O)O
methanesulfonic acid
C=C(C)OC(C)=O
isopropenyl acetate

Reactivos

Ninguno

Disolventes

Cc1ccccc1
toluene

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturathe resulting mixture was then heated
  2. 2
    Temperaturaunder reflux for 6 hours
  3. 3
    OtroAfter completion of the reaction

Procedimiento

To a mixture of 19 g (0.05 mol) of cholesta-1,4,6-trien-3-one (I), 4.8 g (0.05 mol) of methanesulfonic acid and 200 g (2 mol) of isopropenyl acetate were added 200 ml of toluene, and the resulting mixture was then heated under reflux for 6 hours. After completion of the reaction, the same treatment as in Example 1 was carried out to yield 11.7 g of cholesta-1,5,7-trien-3-ol (IV). The yield was 61%.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04723045uspto-grants-1988_02