Reacción #448864

ord-50ef4b395a0e41c98b5d2971079a0e6a

Ecuación de reacción

O=C([O-])O.[Na+]
sodium bicarbonate
Cl
hydrochloric acid
[Br-].[Li+]
lithium bromide
C[C@]12C[C@H](F)[C@H]3[C@@H]([C@H](CCCCCCCl)CC4=CC(=O)CC[C@@H]43)[C@@H]1CCC2=O
7α-(6-chlorohexyl)-11β-fluoro-estr-4-ene-3,17-dione
→
C[C@]12C[C@H](F)[C@@H]3c4ccc(O)cc4C[C@@H](CCCCCCCl)[C@H]3[C@@H]1CCC2=O
7α-(6-chlorohexyl)-11β-fluoro-3-hydroxy-estra-1,3,5(10)-trien-17-one
Rendimiento 22.7%

Reactantes

O=C([O-])O.[Na+]
sodium bicarbonate
Cl
hydrochloric acid
[Br-].[Li+]
lithium bromide
C[C@]12C[C@H](F)[C@H]3[C@@H]([C@H](CCCCCCCl)CC4=CC(=O)CC[C@@H]43)[C@@H]1CCC2=O
7α-(6-chlorohexyl)-11β-fluoro-estr-4-ene-3,17-dione

Reactivos

[Br][Cu][Br]
copper(II) bromide

Disolventes

O
water
CC#N
acetonitrile
CC#N
acetonitrile

Condiciones de reacción

Temperatura
0°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Extracciónextracted 3 times with ethyl acetate
  2. 2
    Lavadowashed with common salt solution
  3. 3
    Otrodried on magnesium sulfate
  4. 4
    Concentraciónconcentrated by evaporation in a vacuum

Procedimiento

28.1 g of copper(II) bromide and 5.4 g of lithium bromide in 105 ml of anhydrous acetonitrile are added to 25.2 g of 7α-(6-chlorohexyl)-11β-fluoro-estr-4-ene-3,17-dione in 175 ml of anhydrous acetonitrile at 80° C. After 15 minutes, the reaction mixture is cooled to 0° C., and 250 ml of saturated sodium bicarbonate solution is added in drops. Then, the solution is stirred into 1 liter of water, brought to pH=6 with 2N hydrochloric acid, extracted 3 times with ethyl acetate, washed with common salt solution, dried on magnesium sulfate and concentrated by evaporation in a vacuum. Chromatography of the crude product on silica gel with a hexane-ethyl acetate gradient yields 5.7g of 7α-(6-chlorohexyl)-11β-fluoro-3-hydroxy-estra-1,3,5(10)-trien-17-one as a foam.

Fuente

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