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

HRID 1834928
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HRID 1834928 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 the 1,5-androstadiene-3β,17β-diol so prepared in a mixture of dry ether and glyme is added zinc-copper couple and methylene iodide. The mixture is refluxed for a period of about 4 hours, cooled to room temperature, diluted with ether and filtered. The filtrate is washed with an aqueous sodium chloride solution, 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. temperatureThe mixture is refluxed for a period of about 4 hours
  2. filtrationfiltered
  3. washThe filtrate is washed with an aqueous sodium chloride solution, 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-8078802cc3cb413d86d31cab6e21f86a
출처 데이터셋
uspto-grants-1978_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04071624

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