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

HRID 1518256Notes

Reaction equation

HRID 1518256 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-0824208dfdc04252b8b9f777c256b993
Source dataset
uspto-grants-2012_07
Patent number
US08232390B2

Reaction notes

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