Sodium periodate → 3,3-(Ethylenedioxy)-11beta-[4'-(methylsulfinyl)[1,1'-biphenyl]-4-yl]-5-estren-17-one

HRID 1654423Notes

Reaction equation

HRID 1654423 reaction equation
[CH2:1]1[CH2:37][O:36][C:3]2([CH2:20][CH2:19][C@H:18]3[C:5](=[CH:6][CH2:7][C@@H:8]4[C@@H:17]3[C@@H:16]([C:21]3[CH:26]=[CH:25][C:24]([C:27]5[CH:32]=[CH:31][C:30]([S:33][CH3:34])=[CH:29][CH:28]=5)=[CH:23][CH:22]=3)[CH2:15][C@@:13]3([CH3:14])[C@H:9]4[CH2:10][CH2:11][C:12]3=[O:35])[CH2:4]2)[O:2]1.I([O-])(=O)(=O)=[O:39].[Na+]>O1CCCC1.CO.O>[CH2:37]1[CH2:1][O:2][C:3]2([CH2:20][CH2:19][C@H:18]3[C:5](=[CH:6][CH2:7][C@@H:8]4[C@@H:17]3[C@@H:16]([C:21]3[CH:26]=[CH:25][C:24]([C:27]5[CH:28]=[CH:29][C:30]([S:33]([CH3:34])=[O:39])=[CH:31][CH:32]=5)=[CH:23][CH:22]=3)[CH2:15][C@@:13]3([CH3:14])[C@H:9]4[CH2:10][CH2:11][C:12]3=[O:35])[CH2:4]2)[O:36]1

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 677883793,3-(Ethylenedioxy)-11beta-[4'-(methylthio)[1,1'-biphenyl]-4-yl]-5-estren-17-one

Product 1

HCID 677891703,3-(Ethylenedioxy)-11beta-[4'-(methylsulfinyl)[1,1'-biphenyl]-4-yl]-5-estren-17-oneYield 67.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

494 mg of 3,3-(ethylenedioxy)-11β-[4'-(methylthio)[1,1'-biphenyl]-4-yl]-5-estren-17-one is dissolved in a mixture of 6 ml of tetrahydrofuran, 6 ml of methanol and 2 ml of water and mixed with 924 mg of sodium periodate. The reaction mixture is stirred at room temperature overnight, then filtered on Celite and the filtrate is diluted with ethyl acetate. The organic phase is washed with saturated sodium bicarbonate solution, dried on sodium sulfate and concentrated by evaporation in a vacuum. After chromatography of the residue on silica gel with a mixture of hexane/ethyl acetate, 346 mg of the title compound is obtained as white foam.

Workup

  1. filtrationfiltered on Celite
  2. additionthe filtrate is diluted with ethyl acetate
  3. washThe organic phase is washed with saturated sodium bicarbonate solution
  4. customdried on sodium sulfate
  5. concentrationconcentrated by evaporation in a vacuum
  6. additionAfter chromatography of the residue on silica gel with a mixture of hexane/ethyl acetate

Sources & evidence

ORD record
ord-a8d1fc59484c435c96448e6043773fbb
Source dataset
uspto-grants-1995_04
Patent number
US05405979

Reaction notes

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