2,5-Hexanedione → Ethyl 5,8-dimethylcarbazole-4-carboxylate

HRID 1197170

Reaktionsgleichung

Reaktionsgleichung von HRID 1197170
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:4]=2[CH:3]=[CH:2]1.[CH2:15]([CH2:19][C:20](=O)[CH3:21])[C:16]([CH3:18])=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH3:21][C:20]1[CH:19]=[CH:15][C:16]([CH3:18])=[C:2]2[C:3]=1[C:4]1[C:5]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=[CH:8][C:9]=1[NH:1]2

Komponenten

5

Edukt 3

HCID 80352,5-HexanedioneHCID 521998p-Toluenesulfonic acid monohydrateHCID 605034Ethyl indole-4-carboxylate

Produkt 1

HCID 19897884Ethyl 5,8-dimethylcarbazole-4-carboxylateAusbeute 39,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 13.24 g of ethyl indole-4-carboxylate, 15.98 g of acetonylacetone and 13.31 g of p-toluenesulfonic acid monohydrate in 50 ml of ethanol was refluxed for 10 hours. The ethanol was evaporated under reduced pressure, the residue was chromatographed on silica gel column with hexane - ethyl acetate (9 : 1) to give 7.45 g of ethyl 5,8-dimethylcarbazole-4-carboxylate.

Aufarbeitung

  1. temperaturewas refluxed for 10 hours
  2. customThe ethanol was evaporated under reduced pressure
  3. customthe residue was chromatographed on silica gel column with hexane - ethyl acetate (9 : 1)

Quellen und Nachweise

ORD-Eintrag
ord-7011647797124f60ab76be0535658e02
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05116995

Verknüpfte Notizen

Wird geladen…