Réaction #93009

ord-6ce408e79760438eb42ae9b3d072b4b6

Équation de réaction

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
O=C(O)C1CCCC1
cyclopentanecarboxylic acid
[Na+].[OH-]
NaOH
O
water
→
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)C1CCCC1
above-identified compound
Rendement 106.6%
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)C1CCCC1
16β-Ethyl-17β-cyclopentanecarbonyloxyacetoxy-4-estren-3-one
Rendement 106.6%

Réactifs

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
O=C(O)C1CCCC1
cyclopentanecarboxylic acid
[Na+].[OH-]
NaOH
O
water

Réactifs

Aucun

Solvants

CC(C)=O
acetone

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    workup.ADDITIONare added
  2. 2
    TempératureThe mixture is refluxed for 6 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
    AutreThe organic layer is separated
  6. 6
    Lavagewashed with water and saturated aqueous sodium chloride solution
  7. 7
    Séchagedried over anhydrous magnesium sulfate
  8. 8
    workup.DISTILLATIONThe solvent is then distilled off under reduced pressure
  9. 9
    LavageAfter serial passage of diisopropyl ether-n-hexane mixtures (1:9, 200 ml; 2:8, 200 ml; and 3:7, 200 ml), elution
  10. 10
    workup.ADDITIONis carried out with 800 ml of a 1:1 mixture of the same solvents
  11. 11
    AutreThe eluate is evaporated under reduced pressure
  12. 12
    Autreto remove the solvent

Mode opératoire

In 40 ml of acetone is dissolved 0.6 g of cyclopentanecarboxylic acid, and 6.0 ml of 1N-NaOH and 16 ml of water are added, followed by addition of 1.2 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one. The mixture is refluxed for 6 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. After serial passage of diisopropyl ether-n-hexane mixtures (1:9, 200 ml; 2:8, 200 ml; and 3:7, 200 ml), elution is carried out with 800 ml of a 1:1 mixture of the same solvents. The eluate is evaporated under reduced pressure to remove the solvent, giving 1.38 g of the above-identified compound as a colorless viscous oil.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US04609650uspto-grants-1986_09