Reaction #92985

ord-ab8880ad3c3d43c197892aa0c3e76e6b

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(=O)[O-].[K+]
potassium acetate
→
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(C)=O
above-identified compound
Yield 35.1%
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(C)=O
16β-Ethyl-17β-acetoxyacetoxy-4-estren-3-one
Yield 35.1%

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(=O)[O-].[K+]
potassium acetate

Reagents

None

Solvents

CC(C)=O
acetone
O
water

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.DISTILLATIONThe acetone is distilled off under reduced pressure
  2. 2
    Extractionthe residue is extracted with 150 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 then distilled off under reduced pressure
  7. 7
    Washpassage of 700 ml of diisopropyl ether-n-hexane (1:1), elution
  8. 8
    workup.ADDITIONis carried out with 600 ml of a 3:2 mixture and 300 ml of a 5:1 mixture of the same solvents
  9. 9
    Otherevaporated under reduced pressure
  10. 10
    Otherto remove the solvent

Procedure

A mixture of 2.1 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one and 1.0 g of potassium acetate is stirred in a mixture of 50 ml of acetone and 3 ml of water for 20 hours. The acetone 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 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 700 ml of diisopropyl ether-n-hexane (1:1), elution is carried out with 600 ml of a 3:2 mixture and 300 ml of a 5:1 mixture of the same solvents. The eluates are combined and evaporated under reduced pressure to remove the solvent, giving 0.7 g of the above-identified compound as colorless crystals.

Source

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