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

HRID 1654423
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HRID 1654423 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water
용매
HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a8d1fc59484c435c96448e6043773fbb
출처 데이터셋
uspto-grants-1995_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05405979

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