Acetyl chloride → methyl 3-acetyl-1-butyl-1H-indole-6-carboxylate

HRID 349012

Reaktionsgleichung

Reaktionsgleichung von HRID 349012
[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[CH:12]=2)[CH:7]=[CH:6]1)[CH2:2][CH2:3][CH3:4].[Cl-].C([Al+]CC)C.[C:24](Cl)(=[O:26])[CH3:25]>ClCCl>[C:24]([C:7]1[C:8]2[C:13](=[CH:12][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:9]=2)[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH:6]=1)(=[O:26])[CH3:25]

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 16686102Diethyl aluminum chlorideHCID 21086134methyl 1-butyl-1H-indole-6-carboxylate

Produkt 1

HCID 21086157methyl 3-acetyl-1-butyl-1H-indole-6-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Methyl 1-butyl-1H-indole-6-carboxylate (4.53 g) was dissolved in dichloromethane (25 ml). The mixture was cooled to 0° C. Diethyl aluminum chloride was added dropwise (29.5 mL) and the mixture was allowed to stir at 0° C. for 30 min. A solution of dichloromethane (25 mL) and acetyl chloride (2.1 mL) was added dropwise, and the mixture was stirred for 2 h at 0° C. The mixture was then partitioned between dichloromethane, water, and brine, dried over sodium sulfate, filtered, and concentrated. The concentrate was chromatographed on silica gel using ethyl acetate/heptane (40/60) to give methyl 3-acetyl-1-butyl-1H-indole-6-carboxylate (3.38 g). MS (ESI+) for C16H19N1O3+H1 m/z 274.14 (M+H)+.

Aufarbeitung

  1. stirringthe mixture was stirred for 2 h at 0° C
  2. customThe mixture was then partitioned between dichloromethane, water, and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-b96b2dd042e04d8088497e16dbbf655d
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176242B2

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