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

HRID 2405845노트

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HRID 2405845 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
65 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3d6471831bbe476c9e58b9a7f244e20e
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08809267B2

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