Sodium Hydroxide → 3-acetyl-1-butyl-1H-indole-6-carboxylic acid

HRID 349013

Reaktionsgleichung

Reaktionsgleichung von HRID 349013
[C:1]([C:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([O:15]C)=[O:14])=[CH:10][CH:11]=2)[N:6]([CH2:17][CH2:18][CH2:19][CH3:20])[CH:5]=1)(=[O:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([C:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([OH:15])=[O:14])=[CH:10][CH:11]=2)[N:6]([CH2:17][CH2:18][CH2:19][CH3:20])[CH:5]=1)(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 14798Sodium Hydroxide2×HCID 21086157methyl 3-acetyl-1-butyl-1H-indole-6-carboxylate

Produkt 1

HCID 210857003-acetyl-1-butyl-1H-indole-6-carboxylic acidAusbeute 84,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

Methyl 3-acetyl-1-butyl-1H-indole-6-carboxylate (2.00 g) was dissolved in methanol (100 mL). Sodium hydroxide (1N) was added until the mixture became slightly cloudy. Methanol was again added (20 mL) until the solution was clear. Sodium hydroxide was again added until the mixture was slightly cloudy. The mixture was allowed to stir at room temperature overnight. The solution was concentrated to half its original volume and hydrochloric acid (2N) was added until the aqueous layer indicated a pH of about one. The mixture was extracted with dichloromethane and the organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated. The resulting material was chromatographed on silica gel using MeOH/heptane/dichloromethane (4/20/76) to give 3-acetyl-1-butyl-1H-indole-6-carboxylic acid (1.60 g). MS (ESI+) for C15H17N1O3+H1 m/z 260.13 (M+H)+.

Aufarbeitung

  1. concentrationThe solution was concentrated to half its original volume and hydrochloric acid (2N)
  2. additionwas added until the aqueous layer
  3. extractionThe mixture was extracted with dichloromethane
  4. washthe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting material was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-ccba24eea716463ab331d697df16cfda
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176242B2

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