Ammonium Acetate → 2-{2-[4-(beta-D-Galactopyranosyloxy)-3-methoxyphenyl]-vinyl}-1-methylquinolinium iodide

HRID 1588200Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1588200
[O:1]([C:13]1[CH:18]=[CH:17][C:16]([CH:19]=O)=[CH:15][C:14]=1[O:21][CH3:22])[C@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4].[I-:23].[CH3:24][N+:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][C:26]=1[CH3:35].C([O-])(=O)C.[NH4+].C(Cl)(Cl)Cl.CO>C(O)C>[I-:23].[C@@H:2]1([O:1][C:13]2[CH:18]=[CH:17][C:16]([CH:19]=[CH:35][C:26]3[CH:27]=[CH:28][C:29]4[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=4)[N+:25]=3[CH3:24])=[CH:15][C:14]=2[O:21][CH3:22])[O:10][C@H:9]([CH2:11][OH:12])[C@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4]

Komponenten

6

Edukt 4

HCID 517165Ammonium AcetateHCID 2750445Quinolinium, 1,2-dimethyl-, iodideHCID 115151674-O-(alpha-d-galactopyranosyl)vanillinHCID 21584188Chloroform methanol

Produkt 1

HCID 678266262-{2-[4-(beta-D-Galactopyranosyloxy)-3-methoxyphenyl]-vinyl}-1-methylquinolinium iodideAusbeute 74,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A stirred suspension of 4-formyl-2-methoxyphenyl β-D-galactopyranoside (1c)(0.12 g, 0.37 mmol), 1,2-dimethylquinolinium iodide (0.10 g, 0.37 mmol) and ammonium acetate (0.06 g, 0.8 mmol) in ethanol (10 ml) was heated under reflux to give a heterogeneous mixture which soon turned orange. After 1 h, t.l.c. (chloroform-methanol 5:4) indicated that the aldehyde had been fully converted into an almost non-mobile orange product. The solution was cooled, filtered and the collected material was washed thoroughly with ethanol to give (21c)(0.16 g, 72%) as an orange crystalline solid, m.p. 225° C., [α]D -18° (c1, DMSO).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux
  3. customto give a heterogeneous mixture which soon turned orange
  4. temperatureThe solution was cooled
  5. filtrationfiltered
  6. washthe collected material was washed thoroughly with ethanol

Quellen und Nachweise

ORD-Eintrag
ord-e32987a02b464d759996b9cb05f123e5
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05221606

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