Реакция #92989

ord-c0bcc5bcb0684d198df1fd0993d5e832

Уравнение реакции

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

Реактанты

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

Реагенты

Нет

Растворители

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

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    ТемператураThe 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
    Экстракцияfollowed by extraction with 100 ml of ethyl acetate
  5. 5
    ДругоеThe organic layer is separated
  6. 6
    Промывкаwashed with water and saturated aqueous sodium chloride solution
  7. 7
    Сушкаdried over anhydrous sodium sulfate
  8. 8
    workup.DISTILLATIONThe solvent is then distilled off
  9. 9
    Промывкаthe residue is subjected to column chromatography, elution
  10. 10
    ДругоеThe eluate is evaporated under reduced pressure
  11. 11
    Другоеto remove the solvent

Методика

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.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US04609650uspto-grants-1986_09