1,2-Dimethylpyridinium iodide → 2-{2-[4-(beta-D-Galactopyranosyloxy)-3-methoxyphenyl]vinyl}-1-methylpyridinium iodide

HRID 1588203

Reaktionsgleichung

Reaktionsgleichung von HRID 1588203
[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[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH3:31].C[O-].[Na+]>CO>[I-:23].[C@@H:2]1([O:1][C:13]2[CH:18]=[CH:17][C:16]([CH:19]=[CH:31][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][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

5

Edukt 3

HCID 701071,2-Dimethylpyridinium iodideHCID 10942334Sodium MethoxideHCID 115151674-O-(alpha-d-galactopyranosyl)vanillin

Produkt 1

HCID 678266832-{2-[4-(beta-D-Galactopyranosyloxy)-3-methoxyphenyl]vinyl}-1-methylpyridinium iodideAusbeute 54,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

4-formyl-2-methoxyphenyl β-D-galactopyranoside (1c)(0.12 g, 0.38 mmol), 1,2-dimethylpyridinium iodide (0.12 g, 0.51 mmol) and methanolic sodium methoxide (1M, 0.38 ml, 0.38 mmol) in methanol (10 ml) was carefully heated until the reagents had completely dissolved, after which the reaction mixture was allowed to cool to room temperature. A yellow precipitate started to separate after about 2 h. The reaction mixture was left over-night (18 h), after which the precipitate was filtered off and washed well with methanol to give (17c)(0.11 g, 54%) as a fine yellow solid, m.p. 210°-230° C. (decomp.), [α]D -14° (c 1, DMSO).

Aufarbeitung

  1. dissolutionhad completely dissolved
  2. customto separate after about 2 h
  3. filtrationafter which the precipitate was filtered off
  4. washwashed well with methanol

Quellen und Nachweise

ORD-Eintrag
ord-1674df0059ab4fe0ad9e4eede99016d5
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05221606

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