Sodium Caprate → 16beta-Ethyl-17beta-n-decanoyloxyacetoxy-4-estren-3-one

HRID 64714

Reaction equation

HRID 64714 reaction equation
[CH2:1]([C@H:3]1[CH2:8][C@H:7]2[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:5]2([CH3:6])[C@H:4]1[O:22][C:23](=[O:26])[CH2:24]Br)[C@@H:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)[CH3:2].[C:27]([O-:38])(=[O:37])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36].[Na+]>CC(C)=O.O>[CH2:1]([C@H:3]1[CH2:8][C@H:7]2[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:5]2([CH3:6])[C@H:4]1[O:22][C:23](=[O:26])[CH2:24][O:38][C:27](=[O:37])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C@@H:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)[CH3:2]

Participants

4

Reactant 2

HCID 4457968Sodium CaprateHCID 1559376416beta-Ethyl-17beta-bromoacetoxy-4-estren-3-one

Product 1

HCID 7046718216beta-Ethyl-17beta-n-decanoyloxyacetoxy-4-estren-3-oneYield 71.3%

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

To 200 ml of acetone-water (1:1) are added 6.0 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one and 5.2 g of sodium n-decanoate and the mixture is refluxed for 10 hours. The solvent is distilled off under reduced pressure and the residue is extracted with 300 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 under reduced pressure and the residue is subjected to column chromatography. Following passage of 750 ml of diisopropyl ether-n-hexane (1:9), elution is carried out with 1000 ml of a 1:1 mixture of the same solvents. The eluate is evaporated under reduced pressure to remove the solvent, giving 5.2 g of the above-identified compound as a light-yellow viscous oil.

Workup

  1. temperaturethe mixture is refluxed for 10 hours
  2. distillationThe solvent is distilled off under reduced pressure
  3. extractionthe residue is extracted with 300 ml of ethyl acetate
  4. customThe organic layer is separated
  5. washwashed with water and saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent is then distilled off under reduced pressure
  8. washpassage of 750 ml of diisopropyl ether-n-hexane (1:9), elution
  9. additionis carried out with 1000 ml of a 1:1 mixture of the same solvents
  10. customThe eluate is evaporated under reduced pressure
  11. customto remove the solvent

Sources & evidence

ORD record
ord-f1c16560236046729a790a84d862926a
Source dataset
uspto-grants-1986_09
Patent number
US04609650

Linked notes

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