Reaction #92987

ord-cdc3ce81002b4065be101e123cbaec2d

Reaction equation

CC[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]2(COC(=O)CBr)C1
16β-ethyl-bromoacetoxy-4-estren-3-one
CC(C)C(=O)[O-].[K+]
potassium isobutyrate
→
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)C(C)C
above-identified compound
Yield 70.8%
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)C(C)C
16β-Ethyl-17β-isobutyryloxyacetoxy-4-estren-3-one
Yield 70.8%

Reactants

CC[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]2(COC(=O)CBr)C1
16β-ethyl-bromoacetoxy-4-estren-3-one
CC(C)C(=O)[O-].[K+]
potassium isobutyrate

Reagents

None

Solvents

CC(C)=O
acetone
O
water

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturethe solution is refluxed for 6 hours
  2. 2
    workup.DISTILLATIONThe acetone is distilled off under reduced pressure
  3. 3
    Extractionthe residue is extracted with 200 ml of ethyl acetate
  4. 4
    OtherThe organic layer is separated
  5. 5
    Washwashed with water and saturated aqueous sodium chloride
  6. 6
    Dryingdried over anhydrous magnesium sulfate
  7. 7
    workup.DISTILLATIONThe solvent is then distilled off under reduced pressure
  8. 8
    Washpassage of 100 ml of diisopropyl ether, elution
  9. 9
    OtherThe eluate is evaporated under reduced pressure
  10. 10
    Otherto remove the solvent

Procedure

In a mixture of 50 ml of acetone and 10 ml of water are dissolved 1.5 g of 16β-ethyl-bromoacetoxy-4-estren-3-one and 0.8 g of potassium isobutyrate and the solution is refluxed for 6 hours. The acetone is distilled off under reduced pressure and the residue is extracted with 200 ml of ethyl acetate. The organic layer is separated, 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 100 ml of diisopropyl ether, elution is carried out with 300 ml of ethyl ether. The eluate is evaporated under reduced pressure to remove the solvent, giving 1.08 g of the above-identified compound as a viscous oil.

Source

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