Reacción #92989

ord-c0bcc5bcb0684d198df1fd0993d5e832

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
CC(C)CCC(=O)O
4-methylvaleric acid
→
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)COC(=O)CCC(C)C
above-identified compound
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)COC(=O)CCC(C)C
16β-Ethyl-17β-(4-methylvaleryl)oxyacetoxy-4-estren-3-one

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
CC(C)CCC(=O)O
4-methylvaleric acid

Reactivos

Ninguno

Disolventes

CC(C)=O
acetone
[Na+].[OH-]
NaOH

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    TemperaturaThe mixture is refluxed for 6 hours
  2. 2
    workup.DISTILLATIONThe acetone is distilled off under reduced pressure and 10 ml of water
  3. 3
    workup.ADDITIONis added to the residue
  4. 4
    Extracciónfollowed by extraction with 100 ml of ethyl acetate
  5. 5
    OtroThe organic layer is separated
  6. 6
    Lavadowashed with water and saturated aqueous sodium chloride solution
  7. 7
    Secadodried over anhydrous sodium sulfate
  8. 8
    workup.DISTILLATIONThe solvent is then distilled off
  9. 9
    Lavadothe residue is subjected to column chromatography, elution
  10. 10
    OtroThe eluate is evaporated under reduced pressure
  11. 11
    Otroto remove the solvent

Procedimiento

In 35 ml of acetone is dissolved 1.0 ml of 4-methylvaleric acid, and 4.6 ml of 2N-NaOH and then 1.9 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one are added to the above solution. The mixture is refluxed for 6 hours. The acetone is distilled off under reduced pressure and 10 ml of water is added to the residue, followed by extraction with 100 ml of ethyl acetate. The organic layer is separated, washed with water and saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent is then distilled off and the residue is subjected to column chromatography, elution being carried out with 600 ml of diisopropyl ether-n-hexane (1:1). The eluate is evaporated under reduced pressure to remove the solvent, giving 1.3 g of the above-identified compound as a colorless viscous oil.

Fuente

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