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

HRID 78054

反応式

HRID 78054 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-3eb2895945b5409e948905dc8beac549
出典データセット
uspto-grants-2014_09
特許番号
US08841327B2

関連ノート

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