Iodine → HCID 131724404, compound

HRID 2084727Notes

Reaction equation

HRID 2084727 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 74%

Procedure

Iodine (1.27 g, 5 mmol) and 19-nor-4-androstene-3,17-dione (272 mg, 1 mmol) were dissolved in methanol (15 mL), and the resultant mixture was stirred for two hours under cooling in an ice-bath. The temperature of 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 220 mg of the title compound (yield: 74%).

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-00022cddba6049ed869af7716ab79fad
Source dataset
uspto-grants-2004_04
Patent number
US06717002B2

Reaction notes

Loading…