Ethyl Acetate → 1-[2-Amino-3-chloro-4-(2,2-dimethoxy-ethoxy)-phenyl]-ethanone

HRID 1893695ノート

反応式

HRID 1893695 の反応式
[NH2:1][C:2]1[C:7]([Cl:8])=[C:6]([OH:9])[CH:5]=[CH:4][C:3]=1[C:10](=[O:12])[CH3:11].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:19][O:20][CH:21]([O:24][CH3:25])[CH2:22]Br.CCOC(C)=O>CN(C=O)C.O>[NH2:1][C:2]1[C:7]([Cl:8])=[C:6]([O:9][CH2:22][CH:21]([O:24][CH3:25])[O:20][CH3:19])[CH:5]=[CH:4][C:3]=1[C:10](=[O:12])[CH3:11]

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 816722-Bromo-1,1-dimethoxyethaneHCID 574451951-(2-Amino-3-chloro-4-hydroxy-phenyl)-ethanone

生成物 1

HCID 574451961-[2-Amino-3-chloro-4-(2,2-dimethoxy-ethoxy)-phenyl]-ethanone収率 67%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
65 °C

実験手順

1-(2-Amino-3-chloro-4-hydroxyphenyl)ethanone (40 g, 215 mmol) was dissolved in DMF (360 ml). Cesium carbonate (140 g, 430 mmol) was added, followed by bromoacetaldehyde dimethyl acetal (54.5 g, 323 mmol). The mixture was then vigorously stirred at 65° C. for 24 h. Upon cooling to room temperature, EtOAc (1 L) and H2O (1 L) were added to the mixture. The organic layer was extracted with EtOAc (1×400 ml). The combined organic layer was washed with aqueous 3% LiCl solution (2×1 L), brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by silica gel chromatography to give 1-[2-amino-3-chloro-4-(2,2-dimethoxyethoxy)phenyl]-ethanone as a white solid (39 g, 67% yield).

後処理

  1. temperatureUpon cooling to room temperature
  2. extractionThe organic layer was extracted with EtOAc (1×400 ml)
  3. washThe combined organic layer was washed with aqueous 3% LiCl solution (2×1 L), brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-ebdec2ca51ec42b696e215453183bbf0
出典データセット
uspto-grants-2013_08
特許番号
US08513186B2

反応ノート

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