Iodine → HCID 131724404, compound

HRID 2084726Notes

Reaction equation

HRID 2084726 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.S([O-])([O-])(=[O:25])=S.[Na+].[Na+].[CH3:30][OH:31]>>[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:25].[CH3:30][O:31][CH3:3]

Participants

5

Reactant 4

HCID 807IodineHCID 887MethanolHCID 24477Sodium ThiosulfateHCID 92834(+)-Estr-4-ene-3,17-dione

Product 1

HCID 131724404HCID 131724404, compoundYield 81%

Procedure

Iodine (560 mg, 2.2 mmol) and 19-nor-4-androstene-3,17-dione (200 mg, 0.735 mmol) were dissolved in methanol (10 mL), and the resultant mixture was stirred for two hours under cooling in an ice-bath. The mixture was maintained at room temperature, and the mixture was further stirred for 1.5 hours, and subsequently 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 177 mg of the title compound (yield: 81%).

Workup

  1. temperatureunder cooling in an ice-bath
  2. temperaturesubsequently refluxed for one hour
  3. temperatureThe reaction mixture was cooled to room temperature
  4. extractionThe mixture was extracted with chloroform
  5. washthe organic phase was washed sequentially with an aqueous solution of sodium bicarbonate and saturated brine
  6. dry with materialThe washed matter was dried over magnesium sulfate anhydrate
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe residue was purified through silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-b7dbc4d0dd54441a825319dc1ff18ce4
Source dataset
uspto-grants-2004_04
Patent number
US06717002B2

Reaction notes

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