Reacción #448820

ord-ee8c9c667c90491798fcd25e571e0af0

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
7α-(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
7α-(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 7α-(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 ml of water while being cooled with ice, diluted with 31 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: US05866560uspto-grants-1999_02