Reacción #737511

ord-643ebed33d884889868e18645457c839

Ecuación de reacción

O
water
C[C@]12CC[C@H]3[C@@H]([C@H](CCCCCO)CC4=CC(=O)CC[C@@H]43)[C@@H]1CCC2=O
7a-(5-hydroxypentyl)-estr-4-ene-3,17-dione
CC(=O)OC(C)=O
acetic anhydride
→
CC(=O)OCCCCC[C@@H]1CC2=CC(=O)CC[C@@H]2[C@H]2CC[C@]3(C)C(=O)CC[C@H]3[C@H]12
7α-(5-acetoxypentyl)-estr-4-ene-3,17-dione

Reactantes

O
water
C[C@]12CC[C@H]3[C@@H]([C@H](CCCCCO)CC4=CC(=O)CC[C@@H]43)[C@@H]1CCC2=O
7a-(5-hydroxypentyl)-estr-4-ene-3,17-dione
CC(=O)OC(C)=O
acetic anhydride

Reactivos

Ninguno

Disolventes

CCOCC
diethyl ether
c1ccncc1
pyridine

Condiciones de reacción

Temperatura
25°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturawhile being cooled with ice
  2. 2
    Otrothe organic phase is dried
  3. 3
    Concentraciónconcentrated by evaporation
  4. 4
    Lavadoafter washing with sodium bicarbonate solution
  5. 5
    OtroThe residue is chromatographed on silica gel

Procedimiento

A solution of 94 g of crude 7a-(5-hydroxypentyl)-estr-4-ene-3,17-dione in 620 ml of pyridine is slowly mixed with 310 ml of acetic anhydride and stirred for 2 hours at 25° C. Then, it is slowly mixed with 116 mnl of water while being cooled with ice, diluted with 3 l of diethyl ether, the organic phase is dried and concentrated by evaporation after washing with sodium bicarbonate solution. The residue is chromatographed on silica gel, and 84.4 g of 7α-(5-acetoxypentyl)-estr-4-ene-3,17-dione is obtained as oil.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US06271403B1uspto-grants-2001_08