Dimethyl Sulfate → 3,5-dimethoxy-1-phenyl-1H-indole-2-carboxylic acid methyl ester

HRID 653143Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 653143
[CH3:1][O:2][C:3]([C:5]1[N:6]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:7]2[C:12]([C:13]=1[OH:14])=[CH:11][C:10]([O:15][CH3:16])=[CH:9][CH:8]=2)=[O:4].[C:23](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O>[CH3:1][O:2][C:3]([C:5]1[N:6]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:7]2[C:12]([C:13]=1[O:14][CH3:23])=[CH:11][C:10]([O:15][CH3:16])=[CH:9][CH:8]=2)=[O:4]

Komponenten

5

Edukt 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 54696100Methyl 3-hydroxy-5-methoxy-1-phenyl-1H-indole-2-carboxylate

Produkt 1

HCID 545333813,5-dimethoxy-1-phenyl-1H-indole-2-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 10.8 g (0.036 mole) of 3-hydroxy-5-methoxy-1-phenyl-1H-indole-2-carboxylic acid methyl ester [P. C. Unangst and M. E. Carethers, J. Heterocyclic Chem., 21, 709 (1984)] and 5.5 g (0.040 mole) of anhydrous potassium carbonate in 100 ml of acetone was treated with 3.7 ml (4.9 g; 0.039 mole) of dimethyl sulfate. The mixture was stirred and heated at reflux for 16 hours, cooled, and filtered. The filter cake was washed several times with fresh acetone, and the combined filtrates were evaporated (vacuum) to yield a crude residue of 3,5-dimethoxy-1-phenyl-1H-indole-2-carboxylic acid methyl ester.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 16 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. washThe filter cake was washed several times with fresh acetone
  6. customthe combined filtrates were evaporated (vacuum)

Quellen und Nachweise

ORD-Eintrag
ord-14f36e025fe143e5b72819c043dae90b
Quelldatensatz
uspto-grants-1987_06
Patentnummer
US04675332

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