Réaction #92982

ord-b6af3c6a671240c1b9147dbf61ec04fa

Équation de réaction

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
Rendement 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
Rendement 75.2%

Réactifs

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

Réactifs

Aucun

Solvants

CO
methanol

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

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

Mode opératoire

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US04609650uspto-grants-1986_09