Cornforth reagent → (E)-methyl 2-(2-((2,5-dimethyl-4-propionylphenoxy)methyl)phenyl)-3-methoxyacrylate

HRID 1619174ノート

反応式

HRID 1619174 の反応式
[OH:1][CH:2]([C:5]1[C:26]([CH3:27])=[CH:25][C:8]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2/[C:17](=[CH:22]\[O:23][CH3:24])/[C:18]([O:20][CH3:21])=[O:19])=[C:7]([CH3:28])[CH:6]=1)[CH2:3][CH3:4].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>ClCCl>[CH3:28][C:7]1[CH:6]=[C:5]([C:2](=[O:1])[CH2:3][CH3:4])[C:26]([CH3:27])=[CH:25][C:8]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1/[C:17](=[CH:22]\[O:23][CH3:24])/[C:18]([O:20][CH3:21])=[O:19]

参加物

4

反応物 2

HCID 2724130Cornforth reagentHCID 67954688(E)-methyl 2-(2-((4-(1-hydroxypropyl)-2,5-dimethylphenoxy)methyl)phenyl)-3-methoxyacrylate

生成物 1

HCID 67955272(E)-methyl 2-(2-((2,5-dimethyl-4-propionylphenoxy)methyl)phenyl)-3-methoxyacrylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

In 10 mL of dichloromethane, 0.15 g (0.39 mmol) of (E)-methyl 2-(2-((4-(1-hydroxypropyl)-2,5-dimethylphenoxy)methyl)phenyl)-3-methoxyacrylate obtained in Step 2 was reacted with 0.29 g (0.78 mmol) of pyridinium dichromate at room temperature for 2 hours with stirring, followed by filtration through celite. The organic layer was dried over anhydrous magnesium sulfate and filtered after which the solvent was removed by concentration in a vacuum. (E)-methyl 2-(2-((2,5-dimethyl-4-propionylphenoxy)methyl)phenyl)-3-methoxyacrylate was obtained as a brown oil (0.11 g, yield: 71%).

後処理

  1. filtrationfollowed by filtration through celite
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered after which the solvent
  4. customwas removed by concentration in a vacuum

出典と根拠

ORDレコード
ord-8e9b162b79b54b03a1e1aaa1a018a20a
出典データセット
uspto-grants-2014_07
特許番号
US08772290B2

反応ノート

読み込み中…