Ammonium Chloride → 2-tert-Butyl-1H-indole

HRID 401252

Reaktionsgleichung

Reaktionsgleichung von HRID 401252
[CH3:1][C:2]([CH3:14])([CH3:13])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:12])=O.[Li]CCCC.[NH4+].[Cl-]>C1COCC1>[C:2]([C:3]1[NH:5][C:6]2[C:7]([CH:12]=1)=[CH:8][CH:9]=[CH:10][CH:11]=2)([CH3:14])([CH3:13])[CH3:1]

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 27340052,2,2'-TrimethylpropionanilideHCID 178418339Butyllithium

Produkt 1

HCID 5941662-tert-Butyl-1H-indoleAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
15 °C

Versuchsvorschrift

To a solution of 2,2-dimethyl-N-o-tolyl-propionamide (30.0 g, 159 mmol) in dry THF (100 mL) was added dropwise n-BuLi (2.5 M, in hexane, 190 mL) at 15° C. The mixture was stirred overnight at 15° C., cooled in an ice-water bath and treated with saturated NH4Cl solution. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated in vacuum. The residue was purified by column chromatography to give 2-tert-butyl-1H-indole (23.8 g, 88%).

Aufarbeitung

  1. temperaturecooled in an ice-water bath
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-cbcef23d52a5486ca0f2d90ba47bfb92
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741925B2

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