Reaction #92991

ord-fc929792369a463e95c40cc536834624

Reaction equation

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
CCCCCCCC(=O)O
n-octanoic acid
→
CCCCCCCC(=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
CCCCCCCC(=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-n-octanoyloxyacetoxy-4-estren-3-one

Reactants

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
CCCCCCCC(=O)O
n-octanoic acid

Reagents

None

Solvents

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

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONare serially added to the above solution
  2. 2
    TemperatureThe mixture is refluxed for 4 hours
  3. 3
    workup.DISTILLATIONThe solvent is distilled off under reduced pressure
  4. 4
    Extractionthe residue is extracted with 150 ml of ethyl acetate
  5. 5
    OtherThe organic layer is separated
  6. 6
    Washwashed with water and saturated aqueous sodium chloride solution
  7. 7
    Dryingdried over anhydrous magnesium sulfate
  8. 8
    workup.DISTILLATIONThe solvent is then distilled off under reduced pressure
  9. 9
    Washpassage of 50 ml of diisopropyl ether, elution
  10. 10
    OtherThe eluate is evaporated under reduced pressure
  11. 11
    Otherto remove the solvent

Procedure

In 60 ml of acetone is dissolved 1.0 ml of n-octanoic acid, and 3.0 ml of 2N-NaOH, 15 ml of water and 1.8 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one are serially added to the above solution. The mixture is refluxed for 4 hours. The solvent 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 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 diisopropyl ether, elution is carried out with 300 ml of the same solvent. The eluate is evaporated under reduced pressure to remove the solvent, giving 1.7 g of the above-identified compound as a colorless oil.

Source

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