Reaction #92989

ord-c0bcc5bcb0684d198df1fd0993d5e832

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
CC(C)CCC(=O)O
4-methylvaleric acid
→
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(C)C
above-identified compound
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(C)C
16β-Ethyl-17β-(4-methylvaleryl)oxyacetoxy-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
CC(C)CCC(=O)O
4-methylvaleric acid

Reagents

None

Solvents

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

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    TemperatureThe mixture is refluxed for 6 hours
  2. 2
    workup.DISTILLATIONThe acetone is distilled off under reduced pressure and 10 ml of water
  3. 3
    workup.ADDITIONis added to the residue
  4. 4
    Extractionfollowed by extraction with 100 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 sodium sulfate
  8. 8
    workup.DISTILLATIONThe solvent is then distilled off
  9. 9
    Washthe residue is subjected to column chromatography, elution
  10. 10
    OtherThe eluate is evaporated under reduced pressure
  11. 11
    Otherto remove the solvent

Procedure

In 35 ml of acetone is dissolved 1.0 ml of 4-methylvaleric 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 6 hours. The acetone is distilled off under reduced pressure and 10 ml of water is added to the residue, followed by extraction with 100 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 and the residue is subjected to column chromatography, elution being carried out with 600 ml of diisopropyl ether-n-hexane (1:1). The eluate is evaporated under reduced pressure to remove the solvent, giving 1.3 g of the above-identified compound as a colorless viscous oil.

Source

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