Réaction #92990

ord-685484c6284b41cb99dbeb91de9c8807

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
CCC(CC)C(=O)O
2-ethylbutyric acid
→
CCC(CC)C(=O)OCC(=O)O[C@H]1[C@@H](CC)C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@@]21C
above-identified compound
CCC(CC)C(=O)OCC(=O)O[C@H]1[C@@H](CC)C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@@]21C
16β-Ethyl-17β-(2-ethylbutyryl)oxyacetoxy-4-estren-3-one

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
CCC(CC)C(=O)O
2-ethylbutyric acid

Réactifs

Aucun

Solvants

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

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    TempératureThe mixture is refluxed for 3 hours
  2. 2
    workup.DISTILLATIONThe acetone is distilled off under reduced pressure
  3. 3
    Extractionthe residue is extracted with two 100 ml portions of ethyl acetate
  4. 4
    Lavagewashed with water and saturated aqueous sodium chloride
  5. 5
    Séchagedried over anhydrous magnesium sulfate
  6. 6
    workup.DISTILLATIONThe solvent is then distilled off under reduced pressure
  7. 7
    Lavagepassage of 50 ml of ether, elution
  8. 8
    AutreThe eluate is evaporated under reduced pressure
  9. 9
    Autreto remove the solvent

Mode opératoire

In 35 ml of acetone is dissolved 1.0 ml of 2-ethylbutyric 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 3 hours. The acetone is distilled off under reduced pressure and the residue is extracted with two 100 ml portions of ethyl acetate. The organic layers are combined, washed with water and saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The solvent is then distilled off under reduced pressure and the residue is subjected to column chromatography. Following passage of 50 ml of ether, elution is carried out with 300 ml of the same solvent. The eluate is evaporated under reduced pressure to remove the solvent, giving 1.63 g of the above-identified compound as a light-yellow viscous oil.

Source

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