Reacción #93009

ord-6ce408e79760438eb42ae9b3d072b4b6

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
O=C(O)C1CCCC1
cyclopentanecarboxylic 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)COC(=O)C1CCCC1
above-identified compound
Rendimiento 106.6%
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)C1CCCC1
16β-Ethyl-17β-cyclopentanecarbonyloxyacetoxy-4-estren-3-one
Rendimiento 106.6%

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
O=C(O)C1CCCC1
cyclopentanecarboxylic acid
[Na+].[OH-]
NaOH
O
water

Reactivos

Ninguno

Disolventes

CC(C)=O
acetone

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
    workup.DISTILLATIONThe solvent is distilled off under reduced pressure
  4. 4
    Extracciónthe residue is extracted with 150 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 magnesium sulfate
  8. 8
    workup.DISTILLATIONThe solvent is then distilled off under reduced pressure
  9. 9
    LavadoAfter serial passage of diisopropyl ether-n-hexane mixtures (1:9, 200 ml; 2:8, 200 ml; and 3:7, 200 ml), elution
  10. 10
    workup.ADDITIONis carried out with 800 ml of a 1:1 mixture of the same solvents
  11. 11
    OtroThe eluate is evaporated under reduced pressure
  12. 12
    Otroto remove the solvent

Procedimiento

In 40 ml of acetone is dissolved 0.6 g of cyclopentanecarboxylic acid, and 6.0 ml of 1N-NaOH and 16 ml of water are added, followed by addition of 1.2 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one. The mixture is refluxed for 6 hours. The solvent is 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 solution and dried over anhydrous magnesium sulfate. The solvent is then distilled off under reduced pressure and the residue is subjected to column chromatography. After serial passage of diisopropyl ether-n-hexane mixtures (1:9, 200 ml; 2:8, 200 ml; and 3:7, 200 ml), elution is carried out with 800 ml of a 1:1 mixture of the same solvents. The eluate is evaporated under reduced pressure to remove the solvent, giving 1.38 g of the above-identified compound as a colorless viscous oil.

Fuente

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