Reacción #92998

ord-e7605e3a96a64f4e8089c5273357f85c

Ecuación de reacción

CC(C)(C)C(=O)O
pivalic acid
[Na+].[OH-]
NaOH
O
water
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@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)C(C)(C)C
above-identified compound
Rendimiento 87.3%
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)C(C)(C)C
16β-Ethyl-17β-pivaloyloxyacetoxy-4-estren-3-one
Rendimiento 87.3%

Reactantes

CC(C)(C)C(=O)O
pivalic acid
[Na+].[OH-]
NaOH
O
water
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

Reactivos

Ninguno

Disolventes

CCOC(C)=O
ethyl acetate
CC(C)=O
acetone
CN(C)C=O
DMF

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.ADDITIONare added
  2. 2
    Temperaturathe mixture is refluxed for 6 hours
  3. 3
    TemperaturaAfter cooling
  4. 4
    Otrothe organic layer is separated
  5. 5
    ExtracciónThe aqueous layer is is further extracted with 50 ml of ethyl acetate
  6. 6
    Lavadowashed with water and saturated aqueous sodium chloride solution
  7. 7
    Secadodried over anhydrous magnesium sulfate
  8. 8
    workup.DISTILLATIONThe solvent is then distilled off under reduced pressure
  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 20 ml of acetone is dissolved 0.61 g of pivalic acid, and 3.0 ml of 2N-NaOH and 10 ml of water are added. And then, 1.2 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one and 30 ml of DMF are added and the mixture is refluxed for 6 hours. After cooling, 150 ml of ethyl acetate is added and the organic layer is separated. The aqueous layer is is further extracted with 50 ml of ethyl acetate. The organic layers are combined, washed with water and saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent is then distilled off under reduced pressure and the residue is subjected to column chromatography, elution being carried out with 400 ml of diisopropyl ether. The eluate is evaporated under reduced pressure to remove the solvent, giving 1.1 g of the above-identified compound as a colorless viscous oil.

Fuente

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