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Ammonium Chloride → 1-{2-[(6,7-Dimethoxy-4-quinolyl)oxy]-5-methoxyphenyl}-1-propanol

HRID 228519
ノート
印刷プレビュー

反応式

HRID 228519 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:17]=1[CH:18]=[O:19].[CH2:26]([Mg]Br)[CH3:27].[Cl-].[NH4+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:17]=1[CH:18]([OH:19])[CH2:26][CH3:27]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 230782792-[(6,7-Dimethoxy-4-quinolyl)oxy]-5-methoxybenzaldehydeHCID 178418443HCID 178418443、化合物

生成物 1

HCID 577565241-{2-[(6,7-Dimethoxy-4-quinolyl)oxy]-5-methoxyphenyl}-1-propanol収率 49%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

Under an argon atmosphere, 2-[(6,7-dimethoxy-4-quinolyl)oxy]-5-methoxybenzaldehyde (140 mg) was dissolved in tetrahydrofuran (2 ml), and the solution was then cooled to −78° C. A 0.96 M tetrahydrofuran solution (0.7 ml) of ethylmagnesium bromide was added dropwise thereto, and the mixture was stirred at −78° C. for one hr. A saturated aqueous ammonium chloride solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with saturated brine and was dried over anhydrous magnesium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using acetone-hexane to give the title compound (74.5 mg, yield 49%).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was then washed with saturated brine
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. customThe solvent was removed
  5. distillationby distillation under the reduced pressure
  6. customthe residue was purified by thin layer chromatography

出典と根拠

ORDレコード
ord-64f91cf1be294a3e90cb00797c1ef687
出典データセット
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07560558B2

反応ノート

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