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

HRID 1518256
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인쇄 미리보기

반응식

HRID 1518256 반응식
[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]
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참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857
Ethyl Acetate
용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-0824208dfdc04252b8b9f777c256b993
출처 데이터셋
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08232390B2

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