Methane → 2-(1H-indol-3-yl)-5,5-dimethylcyclohexane-1,3-dione

HRID 1162168Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1162168
C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH:13]2[C:18](=[O:19])[CH2:17][C:16]([CH3:21])([CH3:20])[CH2:15][C:14]2=[O:22])=[CH:5]1)(=O)C.CO.[OH-].[Na+].C>O>[NH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH:13]2[C:18](=[O:19])[CH2:17][C:16]([CH3:20])([CH3:21])[CH2:15][C:14]2=[O:22])=[CH:5]1

Komponenten

6

Edukt 4

HCID 297MethaneHCID 887MethanolHCID 14798Sodium HydroxideHCID 7947322-(1-Acetylindol-3-yl)-5,5-dimethylcyclohexane-1,3-dione

Produkt 1

HCID 7944562-(1H-indol-3-yl)-5,5-dimethylcyclohexane-1,3-dioneAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a mixture of 2-(1-acetyl-1H-indol-3-yl)-5,5-dimethylcyclohexane-1,3-dione of Example 1e (74.8 g, 0.25 mol) and methanol (30 mL), a solution of sodium hydroxide (30 g, 0.75 mol) in water (300 mL) was added at room temperature under stirring. The reaction mixture was heated at 60° C. for 2 h under stirring, and then activated charcoal (10 g) and water (300 mL) were added. The mixture was stirred for 10 min, charcoal was filtered off, and the filtrate was acidified with hydrochloric acid to pH 2. The solid product was filtered off, washed with water and dried to give 38.3 g (60%) of the colorless solid; m.p. 173° C.

Aufarbeitung

  1. stirringunder stirring
  2. stirringThe mixture was stirred for 10 min
  3. filtrationcharcoal was filtered off
  4. filtrationThe solid product was filtered off
  5. washwashed with water
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-b5adfcce7aa948ada1da7f230105934d
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07820691B2

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