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

HRID 1588203

반응식

HRID 1588203 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-1674df0059ab4fe0ad9e4eede99016d5
출처 데이터셋
uspto-grants-1993_06
특허 번호
US05221606

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