Water → methyl (4-formyl-2-phenyl-1H-imidazol-1-yl)(phenyl)acetate

HRID 2194668ノート

反応式

HRID 2194668 の反応式
[C:1]1([C:7]2[NH:8][CH:9]=[C:10]([CH:12]=[O:13])[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:21]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:22]([O:24][CH3:25])=[O:23].O>CN(C)C=O>[CH:12]([C:10]1[N:11]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]([CH:21]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:22]([O:24][CH3:25])=[O:23])[CH:9]=1)=[O:13]

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 137806Benzeneacetic acid, alpha-bromo-, methyl esterHCID 178519858HCID 178519858、化合物

生成物 1

HCID 86644403methyl (4-formyl-2-phenyl-1H-imidazol-1-yl)(phenyl)acetate収率 25%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
85 °C

実験手順

To a solution of 2-phenyl-1H-imidazole-4-carbaldehyde (1.73 g) in N,N-dimethylformamide (35 mL) were added potassium carbonate (2.78 g) and methyl bromo(phenyl)acetate (2.53) and the mixture was stirred at 85° C. for 3 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=1:1→3:7) and crystallized from diisopropyl ether to give the title compound as colorless crystals (yield 814 mg, yield 25%).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=1:1→3:7)
  6. customcrystallized from diisopropyl ether

出典と根拠

ORDレコード
ord-d47b0af8215e4fa18ad658a14d154973
出典データセット
uspto-grants-2012_12
特許番号
US08334301B2

反応ノート

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