Methyl iodide → 5-[2-(2-Chloro-5-methoxy-phenyl)-propionyl]-1-methyl-1H-pyridin-2-one

HRID 1096007노트

반응식

HRID 1096007 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10][C:11]([C:13]1[CH:14]=[CH:15][C:16](=[O:20])[N:17]([CH3:19])[CH:18]=1)=[O:12].[H-].[Na+].CI.[C:25](OCC)(=O)C>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH:10]([CH3:25])[C:11]([C:13]1[CH:14]=[CH:15][C:16](=[O:20])[N:17]([CH3:19])[CH:18]=1)=[O:12]

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 666993985-[2-(2-Chloro-5-methoxy-phenyl)-acetyl]-1-methyl-1H-pyridin-2-one

생성물 1

HCID 666992895-[2-(2-Chloro-5-methoxy-phenyl)-propionyl]-1-methyl-1H-pyridin-2-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
40 °C

실험 절차

To a suspension of 5-[2-(2-chloro-5-methoxy-phenyl)-acetyl]-1-methyl-1H-pyridin-2-one (9.35 g) in tetrahydrofuran (110 ml) was added sodium hydride (60% dispersion in mineral oil, 1.35 g) in three portions. The mixture was stirred at 40° C. for 1 h and then placed in an ice bath. Methyl iodide (5.01 g) was added dropwise. The mixture was stirred at 0° C. for 10 min and at room temperature for 2 h. Ethyl acetate was added and the mixture was washed with water and brine. The organic phase was dried (MgSO4), filtered and concentrated to dryness. The residue was washed with cyclohexane, filtered and dried to give the title compound as an off-white solid (9.45 g). MS (m/e)=306.2 [M+H+].

후처리

  1. customplaced in an ice bath
  2. stirringThe mixture was stirred at 0° C. for 10 min and at room temperature for 2 h
  3. washthe mixture was washed with water and brine
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. washThe residue was washed with cyclohexane
  8. filtrationfiltered
  9. customdried

출처 및 근거

ORD 기록
ord-310cf3280a8447438a37dd13dbcad494
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138189B2

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