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

HRID 1390738
ノート
印刷プレビュー

反応式

HRID 1390738 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 10290809Zinc copper couple触媒
HCID 3283
Diethyl Ether
溶媒
2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9e0834e2f38844af8b01ab1d04fa277c
出典データセット
uspto-grants-1979_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04139617

反応ノート

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