Reacción #92994

ord-0682f4085c25476da26e2c16fc402b56

Ecuación de reacción

CC[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]2(C)[C@H]1OC(=O)CBr
16β-ethyl-17β-bromoacetoxy-4-estren-3-one
CCCCCCCCCCCCCCCCCC(=O)[O-].[Na+]
sodium stearate
→
CCCCCCCCCCCCCCCCCC(=O)OCC(=O)O[C@H]1[C@@H](CC)C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@@]21C
above-identified compound
Rendimiento 57.1%
CCCCCCCCCCCCCCCCCC(=O)OCC(=O)O[C@H]1[C@@H](CC)C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@@]21C
16β-Ethyl-17β-stearoyloxyacetoxy-4-estren-3-one
Rendimiento 57.1%

Reactantes

CC[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]2(C)[C@H]1OC(=O)CBr
16β-ethyl-17β-bromoacetoxy-4-estren-3-one
CCCCCCCCCCCCCCCCCC(=O)[O-].[Na+]
sodium stearate

Reactivos

Ninguno

Disolventes

CC(C)=O.O
acetone water

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturathe mixture is refluxed for 4 hours
  2. 2
    Otroto stand at room temperature
  3. 3
    Otro(15°-25° C.) overnight
  4. 4
    workup.DISTILLATIONThe solvent is then distilled off under reduced pressure
  5. 5
    Extracciónthe residue is extracted with 150 ml of ethyl acetate
  6. 6
    OtroThe organic layer is separated
  7. 7
    Lavadowashed with water and saturated aqueous sodium chloride
  8. 8
    Secadodried over anhydrous sodium sulfate
  9. 9
    workup.DISTILLATIONThe solvent is distilled off under reduced pressure
  10. 10
    workup.DISSOLUTIONthe residue is dissolved in 100 ml of ethanol
  11. 11
    workup.ADDITIONTo the solution is added 0.3 g of activated carbon
  12. 12
    Filtraciónthe insoluble material is filtered off
  13. 13
    workup.DISTILLATIONThe solvent is distilled off
  14. 14
    Otroto give a colorless viscous oil, which
  15. 15
    Otroto stand at room temperature
  16. 16
    Otro(15°-25° C.)

Procedimiento

To 150 ml of acetone-water (2:1) are added 1.3 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one and 1.0 g of sodium stearate and the mixture is refluxed for 4 hours and allowed to stand at room temperature (15°-25° C.) overnight. The solvent is then distilled off under reduced pressure and the residue is extracted with 150 ml of ethyl acetate. The organic layer is separated, washed with water and saturated aqueous sodium chloride and dried over anhydrous sodium sulfate. The solvent is distilled off under reduced pressure and the residue is dissolved in 100 ml of ethanol. To the solution is added 0.3 g of activated carbon and the insoluble material is filtered off. The solvent is distilled off to give a colorless viscous oil, which is allowed to stand at room temperature (15°-25° C.) to give 1.1 g of the above-identified compound as a solid.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04609650uspto-grants-1986_09