Dimethylformamide → 3-Fluoro-4-(pyridin-2-ylmethoxy)-benzaldehyde

HRID 78054

반응식

HRID 78054 반응식
CN(C)C=O.[OH:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1.[H-].[Na+].[F:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=1F)[CH:20]=[O:21]>O>[F:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=1[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[CH:20]=[O:21]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11474PiconolHCID 24758Sodium hydrideHCID 5880883,4-Difluorobenzaldehyde

생성물 1

HCID 592552243-Fluoro-4-(pyridin-2-ylmethoxy)-benzaldehyde수율 45.6%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To an N,N-dimethylformamide (40.0 mL) solution of 2-(hydroxymethyl)-pyridine (3.00 g, 27.5 mmol) was added sodium hydride (1.00 g, 25.0 mmol, 60% in oil) under nitrogen atmosphere at 0° C., which was stirred for 20 minutes at room temperature. 3,4-Difluorobenzaldehyde (4.69 g, 33.0 mmol) was then added at 0° C., and stirred for 20 minutes at room temperature. 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=1:1→2:1) to obtain the title compound (2.90 g, 45.6%).

후처리

  1. stirringstirred for 20 minutes at room temperature
  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=1:1→2:1)

출처 및 근거

ORD 기록
ord-3eb2895945b5409e948905dc8beac549
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841327B2

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