Trifluoroacetic acid → 5-Chloro-2-isobutylindole

HRID 1191645Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1191645
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=1[CH2:15][C:16](=O)[CH2:17][CH:18]([CH3:20])[CH3:19])(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>ClCCl.C(OCC)(=O)C>[Cl:14][C:11]1[CH:10]=[C:9]2[C:8](=[CH:13][CH:12]=1)[NH:7][C:16]([CH2:17][CH:18]([CH3:20])[CH3:19])=[CH:15]2

Komponenten

6

Edukt 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 67684758Tert-butyl[4-chloro-2-(4-methyl-2-oxopentyl)phenyl]carbamate

Produkt 1

HCID 696707885-Chloro-2-isobutylindoleAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl[4-chloro-2-(4-methyl-2-oxopentyl)phenyl]carbamate (280 mg) in dichloromethane (4 mL) was added trifluoroacetic acid (0.7 mL) at room temperature, and the mixture was stirred for 7 hours. The reaction mixture was diluted with ethyl acetate and stopped the reaction by addition of a saturated aqueous sodium hydrogen carbonate solution. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (166 mg).

Aufarbeitung

  1. customthe reaction
  2. washThe organic layer was washed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-71d549ace18d4ff1a4f4b7d1ef86b882
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680120B2

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