Reaction #92986

ord-a8f40c9d274a414588b143f5af3ffad3

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
CCC(=O)[O-].[K+]
potassium propionate
→
CCC(=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
Yield 35.4%
CCC(=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-propionyloxyacetoxy-4-estren-3-one
Yield 35.4%

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
CCC(=O)[O-].[K+]
potassium propionate

Reagents

None

Solvents

CC(C)=O
acetone
O
water

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Concentrationconcentrated under reduced pressure
  2. 2
    ExtractionThe residue is extracted with 200 ml of ethyl acetate
  3. 3
    OtherThe organic layer is separated
  4. 4
    Washwashed with water and saturated aqueous sodium chloride
  5. 5
    Dryingdried over anhydrous magnesium sulfate
  6. 6
    workup.DISTILLATIONThe solvent is distilled off under reduced pressure
  7. 7
    Washpassage of 1000 ml isopropyl ether-n-hexane (2:3), elution
  8. 8
    OtherThe eluate is evaporated under reduced pressure
  9. 9
    Otherto remove the solvent

Procedure

In a mixture of 50 ml of acetone and 12 ml of water are dissolved 2.5 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one and 0.7 g of potassium propionate. The solution is stirred at room temperature (17°-25° C.) for 3 days and concentrated under reduced pressure. 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 distilled off under reduced pressure and the residue is subjected to column chromatography. Following passage of 1000 ml isopropyl ether-n-hexane (2:3), elution is carried out with 2000 ml of the same solvent system. The eluate is evaporated under reduced pressure to remove the solvent, giving 0.87 g of the above-identified compound as white crystals.

Source

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