Potassium isobutyrate → 16beta-Ethyl-17beta-isobutyryloxyacetoxy-4-estren-3-one

HRID 64709Notes

Reaction equation

HRID 64709 reaction equation
[CH2:1]([C@H:3]1[CH2:13][C@H:12]2[C@H:14]3[C@H:23]([CH2:24][CH2:25][C@:5]2([CH2:6][O:7][C:8](=[O:11])[CH2:9]Br)[CH2:4]1)[C@@H:22]1[C:17](=[CH:18][C:19](=[O:26])[CH2:20][CH2:21]1)[CH2:16][CH2:15]3)[CH3:2].[C:27]([O-:32])(=[O:31])[CH:28]([CH3:30])[CH3:29].[K+]>CC(C)=O.O>[CH2:1]([C@H:3]1[CH2:13][C@H:12]2[C@H:14]3[C@H:23]([CH2:24][CH2:25][C@:5]2([CH3:4])[C@H:6]1[O:7][C:8](=[O:11])[CH2:9][O:32][C:27](=[O:31])[CH:28]([CH3:30])[CH3:29])[C@@H:22]1[C:17](=[CH:18][C:19](=[O:26])[CH2:20][CH2:21]1)[CH2:16][CH2:15]3)[CH3:2]

Participants

5

Reactant 2

HCID 23677462Potassium isobutyrateHCID 8674098016beta-Ethyl-bromoacetoxy-4-estren-3-one

Product 1

HCID 7046730716beta-Ethyl-17beta-isobutyryloxyacetoxy-4-estren-3-oneYield 70.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

In a mixture of 50 ml of acetone and 10 ml of water are dissolved 1.5 g of 16β-ethyl-bromoacetoxy-4-estren-3-one and 0.8 g of potassium isobutyrate and the solution is refluxed for 6 hours. The acetone is distilled off under reduced pressure and 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 then distilled off under reduced pressure and the residue is subjected to column chromatography. Following passage of 100 ml of diisopropyl ether, elution is carried out with 300 ml of ethyl ether. The eluate is evaporated under reduced pressure to remove the solvent, giving 1.08 g of the above-identified compound as a viscous oil.

Workup

  1. temperaturethe solution is refluxed for 6 hours
  2. distillationThe acetone is distilled off under reduced pressure
  3. extractionthe residue is extracted with 200 ml of ethyl acetate
  4. customThe organic layer is separated
  5. washwashed with water and saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent is then distilled off under reduced pressure
  8. washpassage of 100 ml of diisopropyl ether, elution
  9. customThe eluate is evaporated under reduced pressure
  10. customto remove the solvent

Sources & evidence

ORD record
ord-cdc3ce81002b4065be101e123cbaec2d
Source dataset
uspto-grants-1986_09
Patent number
US04609650

Reaction notes

Loading…