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

HRID 1588203ノート

反応式

HRID 1588203 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-1674df0059ab4fe0ad9e4eede99016d5
出典データセット
uspto-grants-1993_06
特許番号
US05221606

反応ノート

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