Myristic Acid → 16beta-Ethyl-17beta-myristoyloxyacetoxy-4-estren-3-one

HRID 64715

Reaction equation

HRID 64715 reaction equation
[C:1]([OH:16])(=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C(=O)([O-])[O-].[K+].[K+].[CH2:23]([C@H:25]1[CH2:30][C@H:29]2[C@H:31]3[C@H:40]([CH2:41][CH2:42][C@:27]2([CH3:28])[C@H:26]1[O:44][C:45](=[O:48])[CH2:46]Br)[C@@H:39]1[C:34](=[CH:35][C:36](=[O:43])[CH2:37][CH2:38]1)[CH2:33][CH2:32]3)[CH3:24]>CC(C)=O>[CH2:23]([C@H:25]1[CH2:30][C@H:29]2[C@H:31]3[C@H:40]([CH2:41][CH2:42][C@:27]2([CH3:28])[C@H:26]1[O:44][C:45](=[O:48])[CH2:46][O:15][C:1](=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C@@H:39]1[C:34](=[CH:35][C:36](=[O:43])[CH2:37][CH2:38]1)[CH2:33][CH2:32]3)[CH3:24]

Participants

5

Reactant 3

HCID 11005Myristic AcidHCID 11430Potassium CarbonateHCID 1559376416beta-Ethyl-17beta-bromoacetoxy-4-estren-3-one

Product 1

HCID 7046748616beta-Ethyl-17beta-myristoyloxyacetoxy-4-estren-3-oneYield 63.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 100 ml of 30% aqueous acetone are added 1.0 g of myristic acid and 0.8 g of potassium carbonate, followed by addition of 1.16 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one. The mixture is refluxed for 5 hours. After cooling, the reaction mixture 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 sodium sulfate. The solvent is then distilled off under reduced pressure and the residue is subjected to column chromatography, elution being carried out with 600 ml of toluene-diisopropyl ether (19:1). The eluate is evaporated under reduced pressure to remove the solvent, giving a light-yellow viscous oil. This product is allowed to stand at room temperature (15°-25° C.) to give 1.0 g of the above-identified compound as a solid.

Workup

  1. temperatureThe mixture is refluxed for 5 hours
  2. temperatureAfter cooling
  3. extractionthe reaction mixture is extracted with 150 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. washthe residue is subjected to column chromatography, elution
  9. customThe eluate is evaporated under reduced pressure
  10. customto remove the solvent
  11. customgiving a light-yellow viscous oil
  12. customto stand at room temperature
  13. custom(15°-25° C.)

Sources & evidence

ORD record
ord-4e73e6cc4d934006ac75e1e1b528d289
Source dataset
uspto-grants-1986_09
Patent number
US04609650

Linked notes

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