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Diiodomethane → 1beta,2beta-Methylene-5-androstene-3beta,17beta-diol

HRID 1733105
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HRID 1733105 반응식
[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH2:8][CH:9]=[C:10]4[C@:15]3([CH3:16])[CH:14]=[CH:13][C@H:12]([OH:20])[CH2:11]4)[C@@H:6]1[CH2:5][CH2:4][C@@H:3]2[OH:21].[CH2:22](COC)OC.C(I)I>CCOCC.[Cu].[Zn]>[CH2:22]1[C@@H:13]2[C@H:12]([OH:20])[CH2:11][C:10]3[C@:15]([CH3:16])([C@H:14]12)[C@@H:17]1[C@H:7]([C@H:6]2[C@@:2]([CH2:19][CH2:18]1)([CH3:1])[C@@H:3]([OH:21])[CH2:4][CH2:5]2)[CH2:8][CH:9]=3
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참가 물질

6

반응물 3

HCID 6346DiiodomethaneHCID 80711,2-DimethoxyethaneHCID 571202841,5-Androstadiene-3beta,17beta-diol

생성물 1

HCID 566286851beta,2beta-Methylene-5-androstene-3beta,17beta-diol

시약·촉매·용매 2

HCID 10290809Zinc copper couple촉매HCID 3283Diethyl Ether
용매
2회

실험 절차

To a stirred solution of 1,5-androstadiene-3β,17β-diol in a mixture of dry ether and glyme is added zinc-copper couple and methylene iodide. This reaction mixture is refluxed for 4 hours, cooled to room temperature, diluted with ether and filtered. The filtrate is washed with aqueous sodium chloride, water and dried over anhydrous magnesium sulfate. The ether is removed under reduced pressure and the residue crystallized from acetone-hexane to yield 1β,2β-methylene-5-androstene-3β,17β-diol.

후처리

  1. temperatureThis reaction mixture is refluxed for 4 hours
  2. filtrationfiltered
  3. washThe filtrate is washed with aqueous sodium chloride, water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe ether is removed under reduced pressure
  6. customthe residue crystallized from acetone-hexane

출처 및 근거

ORD 기록
ord-68a3851e9aea48649486b7e6a75502f5
출처 데이터셋
uspto-grants-1980_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04239681

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