Iodine → HCID 131724404, compound

HRID 2084725Notes

Reaction equation

HRID 2084725 reaction equation
II.[CH3:3][C@@:4]12[C:12](=[O:13])[CH2:11][CH2:10][C@H:9]1[C@@H:8]1[CH2:14][CH2:15][C:16]3[C@@H:22]([C@H:7]1[CH2:6][CH2:5]2)[CH2:21][CH2:20][C:18](=[O:19])[CH:17]=3.O=O.S([O-])([O-])(=[O:27])=S.[Na+].[Na+].[C:32](#N)C>CO>[CH3:3][C@@:4]12[C:12](=[O:13])[CH2:11][CH2:10][C@H:9]1[C@@H:8]1[CH2:14][C:15]([C:16]3[CH:17]=[C:18]([OH:19])[CH:20]=[CH:21][C:22]=3[C@H:7]1[CH2:6][CH2:5]2)=[O:27].[CH3:32][O:19][CH3:18]

Participants

7

Reactant 5

HCID 807IodineHCID 977Oxygen2×HCID 6342AcetonitrileHCID 24477Sodium ThiosulfateHCID 92834(+)-Estr-4-ene-3,17-dione

Product 1

HCID 131724404HCID 131724404, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Iodine (508 mg, 2 mmol) and 19-nor-4-androstene-3,17-dione (272 mg, 1 mmol) were dissolved in a mixture of acetonitrile (12 mL) and methanol (3 mL), to thereby form a reaction mixture. The reaction mixture was stirred for two hours while oxygen was introduced (50 mL/min) thereto under cooling in an ice-bath. The resultant mixture was maintained at room temperature, and after stirring of the mixture for a further 1.5 hours, introduction of oxygen was stopped and the mixture was refluxed for one hour. The reaction mixture was cooled to room temperature, and an aqueous solution of sodium thiosulfate was added to the mixture. The mixture was extracted with chloroform, and the organic phase was washed sequentially with an aqueous solution of sodium bicarbonate and saturated brine. The washed matter was dried over magnesium sulfate anhydrate, filtered, and evaporated under reduced pressure. The residue was purified through silica gel column chromatography (chloroform), to thereby yield 230 mg of the title compound (yield: 77%).

Workup

  1. customto thereby form a reaction mixture
  2. additionwas introduced (50 mL/min)
  3. temperatureunder cooling in an ice-bath
  4. temperaturethe mixture was refluxed for one hour
  5. extractionThe mixture was extracted with chloroform
  6. washthe organic phase was washed sequentially with an aqueous solution of sodium bicarbonate and saturated brine
  7. dry with materialThe washed matter was dried over magnesium sulfate anhydrate
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customThe residue was purified through silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-ad5114de5664450bb98d2e8a497630a6
Source dataset
uspto-grants-2004_04
Patent number
US06717002B2

Reaction notes

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