Ethyl trifluoroacetate → 2-(trifluoromethyl)-1H-indole

HRID 1449620

Reaktionsgleichung

Reaktionsgleichung von HRID 1449620
C([Li])CCC.C[Si](C)(C)[NH:8][C:9]1[C:10]([CH3:15])=[CH:11][CH:12]=[CH:13][CH:14]=1.[F:18][C:19]([F:26])([F:25])[C:20](OCC)=O>O>[F:18][C:19]([F:26])([F:25])[C:20]1[NH:8][C:9]2[C:10]([CH:15]=1)=[CH:11][CH:12]=[CH:13][CH:14]=2

Komponenten

5

Edukt 3

HCID 9794Ethyl trifluoroacetateHCID 529195Benzenamine, 2-methyl, mono-TMSHCID 178418339Butyllithium

Produkt 1

HCID 109321242-(trifluoromethyl)-1H-indoleAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A 2.5 M solution of n-butyl lithium in hexanes (8.8 mL, 22 mmole) at room temperature, under N2, is treated with N,N,N'N'-tetramethylethylenediamine (TMEDA) (3.3 mL, 22 mole), stirred at room temperature for 0.5 hour, treated with N-trimethylsilyl-o-toluidine (1.79 g, 10 mmole), heated at reflux temperature for 6 hours, cooled to -78° C., treated with ethyl trifluoroacetate (1.4 mL, 12 mmole) stirred at -78° C. for 0.25 hour, warmed to room temperature, diluted with water and extracted with diethyl ether. The combined extracts are washed sequentially with 1 N HCl and saturated NaHCO3, dried over MgSO4 and concentrated in vacuo to give a residue. The residue is chromatographed using silica gel and 4:1 hexanes:ethyl acetate as eluent to afford the title product as a light yellow solid, mp 104°-106° C. (literature mp 102° C.1), 0.81 g (47% yield), further identified by IR, 1HNMR and 19FNMR analyses.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux temperature for 6 hours
  3. temperaturecooled to -78° C.
  4. stirringstirred at -78° C. for 0.25 hour
  5. temperaturewarmed to room temperature
  6. extractionextracted with diethyl ether
  7. washThe combined extracts are washed sequentially with 1 N HCl and saturated NaHCO3
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customto give a residue
  11. customThe residue is chromatographed

Quellen und Nachweise

ORD-Eintrag
ord-07414dc4d71247edbb5013ed9f62eefb
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05599832

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