Reaktion #92982

ord-b6af3c6a671240c1b9147dbf61ec04fa

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-].[K+]
potassium formate
→
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
above-identified compound
Ausbeute 75.2%
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
Ausbeute 75.2%

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-].[K+]
potassium formate

Reagenzien

Keine

Lösungsmittel

CO
methanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.DISTILLATIONThe solvent is distilled off under reduced pressure and water
  2. 2
    workup.ADDITIONis added to the residue
  3. 3
    ExtraktionThe mixture is extracted with 150 ml of ethyl acetate
  4. 4
    Waschenthe ethyl acetate layer is washed with water and saturated aqueous sodium chloride solution
  5. 5
    Trocknendried over anhydrous magnesium sulfate
  6. 6
    workup.DISTILLATIONThe solvent is then distilled off under reduced pressure
  7. 7
    Sonstigethe resulting crystalline precipitate is recrystallized from diethyl ether-n-hexane (1:2)

Vorschrift

A mixture of 5.0 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one and 5.0 g of potassium formate is refluxed in 100 ml of methanol for 4 hours. The solvent is distilled off under reduced pressure and water is added to the residue. The mixture is extracted with 150 ml of ethyl acetate, and the ethyl acetate layer 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 resulting crystalline precipitate is recrystallized from diethyl ether-n-hexane (1:2) to give 3.2 g of the above-identified compound as colorless crystals.

Quelle

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