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Diiodomethane → 1beta,2beta-Methylene-19-tetrahydropyranyloxy-5-androstene-3beta,17beta-diol

HRID 1390738
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HRID 1390738 반응식
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C@@:9]12[C@@H:26]3[C@H:17]([C@H:18]4[C@@:22]([CH2:24][CH2:25]3)([CH3:23])[C@@H:21]([OH:27])[CH2:20][CH2:19]4)[CH2:16][CH:15]=[C:14]1[CH2:13][C@@H:12]([OH:28])[CH:11]=[CH:10]2.[CH2:29](COC)OC.C(I)I>CCOCC.[Cu].[Zn]>[CH2:29]1[C@@H:11]2[C@H:12]([OH:28])[CH2:13][C:14]3[C@:9]([CH2:8][O:7][CH:2]4[CH2:3][CH2:4][CH2:5][CH2:6][O:1]4)([C@H:10]12)[C@@H:26]1[C@H:17]([C@H:18]2[C@@:22]([CH2:24][CH2:25]1)([CH3:23])[C@@H:21]([OH:27])[CH2:20][CH2:19]2)[CH2:16][CH:15]=3
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참가 물질

6

반응물 3

HCID 6346DiiodomethaneHCID 80711,2-DimethoxyethaneHCID 2280690319-Tetrahydropyranyloxy-1,5-androstadiene-3beta,17beta-diol

생성물 1

HCID 706050941beta,2beta-Methylene-19-tetrahydropyranyloxy-5-androstene-3beta,17beta-diol

시약·촉매·용매 2

HCID 10290809Zinc copper couple촉매
HCID 3283
Diethyl Ether
용매
2회

실험 절차

To a stirred solution of 19-tetrahydropyranyloxy-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 four hours, cooled to room temperature, diluted with ether and filtered. The ether filtrate is washed with an aqueous sodium chloride solution, washed with water, and dried over anhydrous magnesium sulfate. The ether is removed under reduced pressure and the residue which remains is crystallized from an acetone-hexane solution to yield 1β,2β-methylene-19-tetrahydropyranyloxy-5-androstene-3β,17β-diol.

후처리

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

출처 및 근거

ORD 기록
ord-9e0834e2f38844af8b01ab1d04fa277c
출처 데이터셋
uspto-grants-1979_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04139617

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