Reacción #448853

ord-6f5b837967ea4090b3296a6b7f7eda2b

Ecuación de reacción

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
ClC(Cl)(Cl)Cl
carbon tetrachloride
c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenylphosphine
→
C[C@]12C[C@H](F)[C@H]3[C@@H]([C@H](CCCCCCl)CC4=CC(=O)CC[C@@H]43)[C@@H]1CCC2=O
7α-(5-chloropentyl)-11β-fluoro-estr-4-ene-3,17-dione

Reactantes

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
ClC(Cl)(Cl)Cl
carbon tetrachloride
c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenylphosphine

Reactivos

Ninguno

Disolventes

CC#N
acetonitrile

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    ExtracciónThen, it is extracted with water, aqueous sodium bicarbonate and common salt solution
  2. 2
    Otrodried on sodium sulfate
  3. 3
    Concentraciónconcentrated by evaporation in a vacuum
  4. 4
    Otrochromatographed on silica gel with hexane/ethyl acetate

Procedimiento

A solution of 78.7 g of 11β-fluoro-7α-(5-hydroxypentyl)-estr-4-ene-3,17-dione (Example 12e) in 1.41 of carbon tetrachloride and 475 ml of acetonitrile is stirred with 71 g of triphenylphosphine for 8.5 hours at room temperature. Then, it is extracted with water, aqueous sodium bicarbonate and common salt solution, dried on sodium sulfate, concentrated by evaporation in a vacuum and chromatographed on silica gel with hexane/ethyl acetate. 48.0 g of 7α-(5-chloropentyl)-11β-fluoro-estr-4-ene-3,17-dione is obtained as crystals with a melting point of 51°-53° C. [α]D22 =+78.5°(c=0.5% in chloroform).

Fuente

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