Tetrabutylammonium Fluoride → HCID 86637860, Verbindung

HRID 1518259Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1518259
[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

Komponenten

5

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 86637859HCID 86637859, Verbindung

Produkt 1

HCID 86637860HCID 86637860, VerbindungAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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+).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-6062b8e188f14172af590b95d21afcc7
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232390B2

Notizen zur Reaktion

Wird geladen…