Dimethylformamide → 2-Fluoro-4-(pyridin-2-ylmethoxy)benzaldehyde

HRID 78074

반응식

HRID 78074 반응식
CN(C)C=O.[F:6][C:7]1[CH:14]=[C:13]([OH:15])[CH:12]=[CH:11][C:8]=1[CH:9]=[O:10].[H-].[Na+].[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24]Cl>O>[F:6][C:7]1[CH:14]=[C:13]([O:15][CH2:24][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][N:18]=2)[CH:12]=[CH:11][C:8]=1[CH:9]=[O:10]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 23393Picolyl chlorideHCID 24758Sodium hydrideHCID 5872462-Fluoro-4-hydroxybenzaldehyde

생성물 1

HCID 592553212-Fluoro-4-(pyridin-2-ylmethoxy)benzaldehyde수율 40.6%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To an N,N-dimethylformamide (10.0 mL) solution of 2-fluoro-4-hydroxy-benzaldehyde (1.60 g, 11.4 mmol) was added sodium hydride (547 mg, 13.7 mmol, 60% in oil) under nitrogen atmosphere at 0° C., which was stirred for 30 minutes at room temperature. 2-Picolyl chloride (2.80 g, 17.1 mmol) was then added at room temperature and stirred for 1 hour at 70° C. Water was added to the reaction solution at room temperature, which was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and the solvent was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate: heptane=1:3) to obtain the title compound (1.07 g, 40.6%).

후처리

  1. stirringstirred for 1 hour at 70° C
  2. extractionwhich was then extracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. customthe solvent was evaporated under a reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate: heptane=1:3)

출처 및 근거

ORD 기록
ord-1c9e6d52f78342abbcd23dab4ddeea10
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841327B2

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