Dimethylformamide → 4-(Pyridin-3-yloxy)benzaldehyde

HRID 78012ノート

反応式

HRID 78012 の反応式
CN(C)C=O.[OH:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1.F[C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>O>[N:9]1[CH:10]=[CH:11][CH:12]=[C:7]([O:6][C:14]2[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=2)[CH:8]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 79713-HydroxypyridineHCID 11430Potassium CarbonateHCID 680234-Fluorobenzaldehyde

生成物 1

HCID 46774194-(Pyridin-3-yloxy)benzaldehyde収率 27.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

To an N,N-dimethylformamide (30.0 mL) solution of 3-hydroxypyridine (3.00 g, 31.5 mmol) and 4-fluorobenzaldehyde (5.08 g, 41.0 mmol) was added potassium carbonate (8.71 g, 63.0 mmol) under nitrogen atmosphere, which was stirred for 17 hours at 70° C. The reaction mixture was then cooled to room temperature and water was added thereto, followed by extraction 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->3:1) to obtain the title compound (1.70 g, 27.1%).

後処理

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. extractionfollowed by extraction 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->3:1)

出典と根拠

ORDレコード
ord-6fba9d3a83b648ecb0ef8e5d996d8906
出典データセット
uspto-grants-2014_09
特許番号
US08841327B2

反応ノート

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