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Tetrabutylammonium Fluoride → 11beta-(4-Acetylphenyl)-17alpha-hydroxy-17-(2-propinyl)14beta-estra-4,9-dien-3-one

HRID 5338
ノート
印刷プレビュー

反応式

HRID 5338 の反応式
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C@H:10]2[CH2:27][C@@:25]3([CH3:26])[C@H:21]([CH2:22][CH2:23][C@:24]3([OH:35])[CH2:28][C:29]#[C:30][Si](C)(C)C)[C@H:20]3[C:11]2=[C:12]2[C:17]([CH2:18][CH2:19]3)=[CH:16][C:15](=[O:36])[CH2:14][CH2:13]2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C@H:10]2[CH2:27][C@@:25]3([CH3:26])[C@H:21]([CH2:22][CH2:23][C@:24]3([OH:35])[CH2:28][C:29]#[CH:30])[C@H:20]3[C:11]2=[C:12]2[C:17]([CH2:18][CH2:19]3)=[CH:16][C:15](=[O:36])[CH2:14][CH2:13]2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 1462340011beta-(4-Acetylphenyl)-17alpha-hydroxy-17-(3-trimethysilyl-2-propinyl)-14beta-estra-4,9-dien-3-one

生成物 1

HCID 1462340211beta-(4-Acetylphenyl)-17alpha-hydroxy-17-(2-propinyl)14beta-estra-4,9-dien-3-one収率 69.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

470 mg of 11beta-(4-Acetylphenyl)-17alpha-hydroxy-17-(3-trimethysilyl-2-propinyl)-14beta-estra-4,9-dien-3-one in 24 ml of tetrahydrofuran is mixed with 2.35 ml of a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran and stirred for 5 minutes at room temperature. It is poured on water and extracted with ethyl acetate. The combined organic phases are washed with water, dried on sodium sulfate and concentrated by evaporation. The residue is chromatographed with a mixture of hexane/ethyl acetate on silica gel. 280 mg of the title compound is isolated as foam.

後処理

  1. additionIt is poured on water
  2. extractionextracted with ethyl acetate
  3. washThe combined organic phases are washed with water
  4. customdried on sodium sulfate
  5. concentrationconcentrated by evaporation
  6. customThe residue is chromatographed with a mixture of hexane/ethyl acetate on silica gel

出典と根拠

ORDレコード
ord-5496bc558f464336aaaccae32ef16785
出典データセット
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05244886

反応ノート

読み込み中…

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