Tetrabutylammonium Fluoride → HCID 136407108、化合物

HRID 1479933ノート

反応式

HRID 1479933 の反応式
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Si]([O:26][C:27]1[CH:28]=[CH:29][C:30]([C:37]2[CH:42]=[CH:41][C:40]([C:43]3[N:47]([C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)[C:46]4[CH:54]=[CH:55][CH:56]=[CH:57][C:45]=4[N:44]=3)=[CH:39][CH:38]=2)=[C:31]2[C:36]=1[N:35]=[CH:34][CH:33]=[CH:32]2)(C(C)(C)C)(C)C>C1COCC1>[C:48]1([N:47]2[C:46]3[CH:54]=[CH:55][CH:56]=[CH:57][C:45]=3[N:44]=[C:43]2[C:40]2[CH:39]=[CH:38][C:37]([C:30]3[CH:29]=[CH:28][C:27]([OH:26])=[C:36]4[C:31]=3[CH:32]=[CH:33][CH:34]=[N:35]4)=[CH:42][CH:41]=2)[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 67362201HCID 67362201、化合物

生成物 1

HCID 136407108HCID 136407108、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A 1M TBAF solution in THF (22.4 ml, 22.4 mmol) is added dropwise to a solution of 8-(tert-butyldimethylsilanyloxy)-5-[4-(1-phenyl-1H-benzimidazol-2-yl)phenyl]quinoline (7.9 g, 14.90 mmol) in THF (20 ml). After stirring for 4 h, the mixture is washed with 5% aqueous NH4Cl (100 ml) solution and extracted with ethyl acetate (3×50 ml). The combined organic phases are dried over sodium sulfate, and the solvent is removed under reduced pressure. The crude product is purified by flash chromatography on silica and crystallisation from MeOH (5.9 g, 90%).

後処理

  1. washthe mixture is washed with 5% aqueous NH4Cl (100 ml) solution
  2. extractionextracted with ethyl acetate (3×50 ml)
  3. dry with materialThe combined organic phases are dried over sodium sulfate
  4. customthe solvent is removed under reduced pressure
  5. customThe crude product is purified by flash chromatography on silica and crystallisation from MeOH (5.9 g, 90%)

出典と根拠

ORDレコード
ord-d6c024d8e15c48339353664821fc5e92
出典データセット
uspto-grants-2016_08
特許番号
US09409883B2

反応ノート

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