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

HRID 1588203Notes

Reaction equation

HRID 1588203 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 678266832-{2-[4-(beta-D-Galactopyranosyloxy)-3-methoxyphenyl]vinyl}-1-methylpyridinium iodideYield 54.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-1674df0059ab4fe0ad9e4eede99016d5
Source dataset
uspto-grants-1993_06
Patent number
US05221606

Reaction notes

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