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Tetrabutylammonium Fluoride → Methyl 1-allyl-3-cyclohexyl-2-[2-(hydroxymethyl)phenyl]-1H-indole-6-carboxylate

HRID 1518256
ノート
印刷プレビュー

反応式

HRID 1518256 の反応式
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:19]([N:22]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([C:31]([O:33][CH3:34])=[O:32])[CH:29]=2)[C:24]([CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)=[C:23]1[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=1[CH2:47][O:48][Si](C(C)C)(C(C)C)C(C)C)[CH:20]=[CH2:21]>C1COCC1.CCOC(C)=O>[CH2:19]([N:22]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([C:31]([O:33][CH3:34])=[O:32])[CH:29]=2)[C:24]([CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)=[C:23]1[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=1[CH2:47][OH:48])[CH:20]=[CH2:21]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 68703163Methyl 1-allyl-3-cyclohexyl-2-(2-{[(triisopropylsilyl)oxy]methyl}phenyl)-1H-indole-6-carboxylate

生成物 1

HCID 68702775Methyl 1-allyl-3-cyclohexyl-2-[2-(hydroxymethyl)phenyl]-1H-indole-6-carboxylate収率 95%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857
Ethyl Acetate
溶媒

実験手順

Tetrabutylammonium fluoride (1.3 eq., 1M solution in THF) was added dropwise to an ice cooled solution of methyl 1-allyl-3-cyclohexyl-2-(2-{[(triisopropylsilyl)oxy]methyl}phenyl)-1H-indole-6-carboxylate in THF (0.036M). The mixture was stirred at RT for 1 h then diluted with EtOAc, washed with saturated aq. NH4Cl, water and brine. The organic phase was dried over Na2SO4 and evaporated in vacuo. The residual material was subjected to flash chromatography (PE:EtOAc, 4:1). After evaporation of the solvent the product was obtained as colourless solid (95%). MS (ES+): 404.3 (M+H+).

後処理

  1. washwashed with saturated aq. NH4Cl, water and brine
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customevaporated in vacuo
  4. customAfter evaporation of the solvent the product

出典と根拠

ORDレコード
ord-0824208dfdc04252b8b9f777c256b993
出典データセット
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08232390B2

反応ノート

読み込み中…

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