Acetic Acid → 5-(4-methoxy-1H-indol-3-ylmethylene)-2,2-dimethyl-[1,3]dioxane-4,6-dione

HRID 250200

Reaktionsgleichung

Reaktionsgleichung von HRID 250200
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[C:5]([CH:12]=O)=[CH:6][NH:7]2.[CH3:14][C:15]1([CH3:23])[O:22][C:20](=[O:21])[CH2:19][C:17](=[O:18])[O:16]1.N1CCCCC1.C(O)(=O)C>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[C:5]([CH:12]=[C:19]1[C:20](=[O:21])[O:22][C:15]([CH3:23])([CH3:14])[O:16][C:17]1=[O:18])=[CH:6][NH:7]2

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 1462294-Methoxyindole-3-aldehyde

Produkt 1

HCID 580886345-(4-methoxy-1H-indol-3-ylmethylene)-2,2-dimethyl-[1,3]dioxane-4,6-dioneAusbeute 49,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

4-MethoxyIndole-3-carboxaldehyde (5.0 g) and Meldrum's acid (2,2-Dimethyl-[1,3]dioxane-4,6-dione, 4.11 g) were mixed in toluene (200 ml). To this mixture was added 0.6 ml each of piperidine and acetic acid. The reaction mixture was stirred at room temperature for four hours. The precipitate was filtered and washed with toluene to afford 4.25 g of crude 5-(4-methoxy-1H-indol-3-ylmethylene)-2,2-dimethyl-[1,3]dioxane-4,6-dione as an orange solid which was used without further purification.

Aufarbeitung

  1. filtrationThe precipitate was filtered
  2. washwashed with toluene

Quellen und Nachweise

ORD-Eintrag
ord-5ec2ee22f47648618acde918198d5833
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863305B2

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