2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 16alpha-Fluoro-1,6alpha-dimethyl-7-methylenandrosta-1,4-diene-3,17-dione

HRID 621623ノート

反応式

HRID 621623 の反応式
[F:1][C@@H:2]1[CH2:7][C@H:6]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:4]2([CH3:5])[C:3]1=[O:25])[C@:16]1([CH3:17])[C:11](=[CH:12][C:13](=[O:22])[CH2:14][C@H:15]1[CH3:21])[C@@H:10]([CH3:23])[C:9]3=[CH2:24].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[F:1][C@@H:2]1[CH2:7][C@H:6]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:4]2([CH3:5])[C:3]1=[O:25])[C@:16]1([CH3:17])[C:11](=[CH:12][C:13](=[O:22])[CH:14]=[C:15]1[CH3:21])[C@@H:10]([CH3:23])[C:9]3=[CH2:24]

参加物

4

反応物 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 1863203216alpha-Fluoro-1beta,6alpha-dimethyl-7-methylenandrost-4-ene-3,17-dione

生成物 1

HCID 1863203116alpha-Fluoro-1,6alpha-dimethyl-7-methylenandrosta-1,4-diene-3,17-dione収率 64.9%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

A mixture of 16α-fluoro-1β,6α-dimethyl-7-methylenandrost-4-ene-3,17-dione (344 mg) and dichlorodicyanobenzoquinone (363 mg) in dioxane (20 ml) is refluxed for about 15 hours. Then the resulting suspension is cooled, the precipitate filtered off and the filtrate evaporated in vacuo. The residue is dissolved in ethyl acetate, the organic layer washed with water, dried over sodium sulfate and the solvent removed under vacuum. The crude product is chromatographed on silica gel using hexane/ethyl acetate as eluant to yield 16α-fluoro-1,6α-dimethyl-7-methylenandrosta-1,4-diene-3,17-dione (222 mg).

後処理

  1. temperatureis refluxed for about 15 hours
  2. temperatureThen the resulting suspension is cooled
  3. filtrationthe precipitate filtered off
  4. customthe filtrate evaporated in vacuo
  5. dissolutionThe residue is dissolved in ethyl acetate
  6. washthe organic layer washed with water
  7. dry with materialdried over sodium sulfate
  8. customthe solvent removed under vacuum
  9. customThe crude product is chromatographed on silica gel

出典と根拠

ORDレコード
ord-0c2009cd927e49e295afc8433c522396
出典データセット
uspto-grants-1989_04
特許番号
US04824830

反応ノート

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