Tetrabutylammonium Fluoride → 5-Chloro-3-phenyl-7-nitro-1H-indole

HRID 1802825ノート

反応式

HRID 1802825 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[NH:7][C:6]([Si](C)(C)C)=[C:5]2[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

5

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 684760765-Chloro-7-nitro-3-phenyl-2-trimethylsilyl-1H-indole

生成物 1

HCID 684718405-Chloro-3-phenyl-7-nitro-1H-indole収率 101.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

5-Chloro-7-nitro-3-phenyl-2-trimethylsilyl-1H-indole (1.5 g, 4.35 mmol) obtained in Step 2 was dissolved in tetrahydrofurane (30 mL), and 1 M tetrabutylammoniumfluoride solution (5.2 mL, 5.2 mmol) was added in drops at 0° C. At the end of reaction, the resulting mixture was diluted with water and extracted with ethylacetate. The extract was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and filtered. The solvent was removed under reduced pressure and the residue was separated using column chromatography to give 5-chloro-3-phenyl-7-nitro-1H-indole (1.2 g, Yield 100%).

後処理

  1. customAt the end of reaction
  2. extractionextracted with ethylacetate
  3. washThe extract was washed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was separated

出典と根拠

ORDレコード
ord-4599e6e4bc7f485781140124c9c69bd3
出典データセット
uspto-grants-2013_01
特許番号
US08349885B2

反応ノート

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