Dimethylformamide → 3-Fluoro-4-(5-fluoro-pyridin-2-ylmethoxy)-benzaldehyde

HRID 78071

反応式

HRID 78071 の反応式
CN(C)C=O.[F:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][OH:14])=[N:11][CH:12]=1.[H-].[Na+].[F:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][C:25]=1F)[CH:21]=[O:22]>O>[F:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][C:25]=1[O:14][CH2:13][C:10]1[CH:9]=[CH:8][C:7]([F:6])=[CH:12][N:11]=1)[CH:21]=[O:22]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 5880883,4-DifluorobenzaldehydeHCID 24729312(5-Fluoropyridin-2-yl)methanol

生成物 1

HCID 592554743-Fluoro-4-(5-fluoro-pyridin-2-ylmethoxy)-benzaldehyde収率 42.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To an N,N-dimethylformamide (20.0 mL) solution of (5-fluoro-pyridin-2-yl)-methanol (760 mg, 5.98 mmol) described in Manufacturing Example 41-1-1 was added sodium hydride (239 mg, 5.98 mmol, 60% in oil) under nitrogen atmosphere at 0° C., which was stirred for 10 minutes at room temperature. 3,4-Difluorobenzaldehyde (935 mg, 6.58 mmol) was then added at room temperature, and stirred for 30 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=1:3) to obtain the title compound (629 mg, 42.2%).

後処理

  1. stirringstirred for 30 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=1:3)

出典と根拠

ORDレコード
ord-6bbc91011dee41c3900085ff4d95ec9c
出典データセット
uspto-grants-2014_09
特許番号
US08841327B2

関連ノート

読み込み中…