Tetrabutylammonium Fluoride → HCID 86637860, compound

HRID 1518259Notes

Reaction equation

HRID 1518259 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH:19]1([C:25]2[C:33]3[C:28](=[CH:29][C:30]([C:34]([O:36][CH3:37])=[O:35])=[CH:31][CH:32]=3)[N:27]([CH2:38][C:39]#[CH:40])[C:26]=2[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[CH2:47][O:48][Si](C(C)C)(C(C)C)C(C)C)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>C1COCC1.CCOC(C)=O>[CH:19]1([C:25]2[C:33]3[C:28](=[CH:29][C:30]([C:34]([O:36][CH3:37])=[O:35])=[CH:31][CH:32]=3)[N:27]([CH2:38][C:39]#[CH:40])[C:26]=2[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[CH2:47][OH:48])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86637859HCID 86637859, compound

Product 1

HCID 86637860HCID 86637860, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Tetrabutylammonium fluoride (1.3 eq., 1M solution in THF) was added dropwise to an ice cooled solution of methyl 3-cyclohexyl-1-prop-2-yn-1-yl-2-(2-{[(triisopropylsilyl)oxy]methyl}phenyl)-1H-indole-6-carboxylate in THF (0.036M). The mixture was stirred at 0° C. 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, 3:1). After evaporation of the solvents the product was obtained as white solid (63%). MS (ES+): 402.6 (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 solvents the product

Sources & evidence

ORD record
ord-6062b8e188f14172af590b95d21afcc7
Source dataset
uspto-grants-2012_07
Patent number
US08232390B2

Reaction notes

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