Water → 2-cyclohexyl-5-nitro-1H-indole

HRID 1947432ノート

反応式

HRID 1947432 の反応式
[CH:1]1([C:7]2[N:8](S(C)(=O)=O)[C:9]3[C:14]([CH:15]=2)=[CH:13][C:12]([N+:16]([O-:18])=[O:17])=[CH:11][CH:10]=3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O.CCOC(C)=O>C1COCC1>[CH:1]1([C:7]2[NH:8][C:9]3[C:14]([CH:15]=2)=[CH:13][C:12]([N+:16]([O-:18])=[O:17])=[CH:11][CH:10]=3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

参加物

6

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 672853302-cyclohexyl-1-(methylsulfonyl)-5-nitro-1H-indole

生成物 1

HCID 672849682-cyclohexyl-5-nitro-1H-indole収率 72.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution containing 2-cyclohexyl-1-(methylsulfonyl)-5-nitro-1H-indole (5.8 g; 18 mmol) in THF (50 ml), tetrabutylammonium fluoride (1M solution in THF; 18 ml; 18 mmol) was added dropwise. The reaction mixture was refluxed for 18 hours, then cooled to room temperature. Water (50 ml) and EtOAc (50 ml) were added, the biphasic solution was transferred into a separating funnel, the organic layer separated and dried over Na2SO4, and the solvent was removed by evaporation under reduced pressure. The residue was purified by flash chromatography on silica gel (n-hexane/EtOAc, n-hexane 100→80%) to give 2-cyclohexyl-5-nitro-1H-indole (3.2 g), which was used without any further purification.

後処理

  1. additionwas added dropwise
  2. temperatureThe reaction mixture was refluxed for 18 hours
  3. customthe biphasic solution was transferred into a separating funnel
  4. customthe organic layer separated
  5. dry with materialdried over Na2SO4
  6. customthe solvent was removed by evaporation under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel (n-hexane/EtOAc, n-hexane 100→80%)

出典と根拠

ORDレコード
ord-3ba1acb5b6b84b8493d18d2e275579d8
出典データセット
uspto-grants-2013_03
特許番号
US08399477B2

反応ノート

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