Reaktion #92997

ord-ba43561350ab4dbdae794445f8174128

Reaktionsgleichung

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-])CCC(=O)O.[Na+]
monosodium succinate
→
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(=O)O
above-identified compound
Ausbeute 24.5%
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(=O)O
16β-Ethyl-17β-(2-carboxyethyl)carbonyloxyacetoxy-4-estren-3-one
Ausbeute 24.5%

Edukte

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-])CCC(=O)O.[Na+]
monosodium succinate

Reagenzien

Keine

Lösungsmittel

CC(C)=O
acetone

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.DISTILLATIONThe acetone is distilled off under reduced pressure
  2. 2
    Extraktionthe residue is extracted with 150 ml of ethyl acetate
  3. 3
    SonstigeThe organic layer is separated
  4. 4
    Waschenwashed with water and saturated aqueous sodium chloride solution
  5. 5
    Trocknendried over anhydrous sodium sulfate
  6. 6
    workup.DISTILLATIONThe solvent is then distilled off under reduced pressure
  7. 7
    Waschenpassage of 450 ml of chloroform, elution
  8. 8
    SonstigeThe eluate is evaporated under reduced pressure
  9. 9
    Sonstigeto remove the solvent
  10. 10
    Sonstigegiving colorless crystals
  11. 11
    WaschenThe product is washed with petroleum ether
  12. 12
    Sonstigedried

Vorschrift

In 100 ml of 50% aqueous acetone are dissolved 1.5 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one and 0.7 g of monosodium succinate and the solution is stirred at room temperature (15°-25° C.) for 3 days. The acetone 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 sodium sulfate. The solvent is then distilled off under reduced pressure and the residue is subjected to column chromatography. Following passage of 450 ml of chloroform, elution is carried out with 150 ml of ethyl acetate. The eluate is evaporated under reduced pressure to remove the solvent, giving colorless crystals. The product is washed with petroleum ether and dried to give 0.4 g of the above-identified compound.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04609650uspto-grants-1986_09