Reacción #448840

ord-69b7ec4e811a454ba13044aded6aab0b

Ecuación de reacción

O
water
C[C@]12C[C@H](F)[C@H]3[C@@H]([C@H](CCCCCO)CC4=CC(=O)CC[C@@H]43)[C@@H]1CCC2=O
11β-fluoro-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]2[C@@H]1[C@@H]1CCC(=O)[C@@]1(C)C[C@@H]2F
7α-(5-acetoxypentyl)-11β-fluoro-estr-4-ene-3,17-dione

Reactantes

O
water
C[C@]12C[C@H](F)[C@H]3[C@@H]([C@H](CCCCCO)CC4=CC(=O)CC[C@@H]43)[C@@H]1CCC2=O
11β-fluoro-7α-(5-hydroxypentyl)-estr-4-ene-3,17-dione
CC(=O)OC(C)=O
acetic anhydride

Reactivos

Ninguno

Disolventes

c1ccncc1
pyridine

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    ExtracciónIt is extracted with diethyl ether
  2. 2
    Lavadowashed with 2N sulfric acid, pyridine-free
  3. 3
    OtroAfter drying
  4. 4
    Concentraciónconcentration
  5. 5
    Otroby evaporation in a vacuum
  6. 6
    Otrothe crude product is chromatographed on silica gel with a hexane-ethyl acetate-gradient

Procedimiento

20 g of 11β-fluoro-7α-(5-hydroxypentyl)-estr-4-ene-3,17-dione in 100 ml of pyridine can be reacted over a period of 2 hours with 50 ml of acetic anhydride at 25° C. Then, 5 ml of water is added at 0° C., and it is stirred for 45 minutes. It is extracted with diethyl ether, washed with 2N sulfric acid, pyridine-free, and the solution is neutralized in succession with saturated sodium bicarbonate solution and water. After drying and concentration by evaporation in a vacuum, the crude product is chromatographed on silica gel with a hexane-ethyl acetate-gradient. 17 g of 7α-(5-acetoxypentyl)-11β-fluoro-estr-4-ene-3,17-dione with a melting point of 78.4° C. is obtained.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05866560uspto-grants-1999_02