Reacción #93004

ord-a12a091f133c40afb685201a87e3a710

Ecuación de reacción

CCOC(C)=O
ethyl acetate
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)CO
16β-ethyl-17β-glycoloyloxy-4-estren-3-one
CC(=O)[O-].[Na+]
sodium acetate
C=C1CC(=O)O1
diketene
→
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)CC(C)=O
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)CC(C)=O
16β-Ethyl-17β-(3-oxobutyryl)oxyacetoxy-4-estren-3-one

Reactantes

CCOC(C)=O
ethyl acetate
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)CO
16β-ethyl-17β-glycoloyloxy-4-estren-3-one
CC(=O)[O-].[Na+]
sodium acetate
C=C1CC(=O)O1
diketene

Reactivos

Ninguno

Disolventes

ClCCl
dichloromethane

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.ADDITIONare added
  2. 2
    TemperaturaThe mixture is refluxed for 4 hours
  3. 3
    TemperaturaAfter cooling
  4. 4
    Lavadothe mixture is washed with water and saturated aqueous sodium chloride solution
  5. 5
    Secadodried over anhydrous magnesium sulfate
  6. 6
    workup.DISTILLATIONThe solvent is then distilled off under reduced pressure
  7. 7
    Lavadopassage of 400 ml of diisopropyl ether and 400 ml of diisopropyl ether-ethyl acetate (10:1), elution
  8. 8
    OtroThe eluate is evaporated under reduced pressure
  9. 9
    Otroto remove the solvent

Procedimiento

In 30 ml of dichloromethane is dissolved 0.8 g of 16β-ethyl-17β-glycoloyloxy-4-estren-3-one, and 0.24 g of anhydrous sodium acetate and 0.3 ml of diketene are added. The mixture is refluxed for 4 hours. After cooling, 100 ml of ethyl acetate is added and the mixture is 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. Following serial passage of 400 ml of diisopropyl ether and 400 ml of diisopropyl ether-ethyl acetate (10:1), elution is carried out with 600 ml of isopropyl ether-ethyl acetate (2:3). The eluate is evaporated under reduced pressure to remove the solvent, giving 1.0 g of the above-identified compound as a light-yellow viscous oil.

Fuente

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