Dimethylformamide → (4-(Pyridin-2-yloxymethyl)-phenyl)-methanol

HRID 77799

反応式

HRID 77799 の反応式
[C:1]1([CH2:9][OH:10])[CH:6]=[CH:5][C:4]([CH2:7][OH:8])=[CH:3][CH:2]=1.F[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.CN(C)C=O.[H-].[Na+]>O>[N:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[O:8][CH2:7][C:4]1[CH:5]=[CH:6][C:1]([CH2:9][OH:10])=[CH:2][CH:3]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 97462-FluoropyridineHCID 115061,4-BenzenedimethanolHCID 24758Sodium hydride

生成物 1

HCID 59255473(4-(Pyridin-2-yloxymethyl)-phenyl)-methanol収率 67.9%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

To a mixture of 1,4-benzenedimethanol (5.5 g, 40 mmol), 2-fluoropyridine (1.3 g, 13 mmol) and N,N-dimethylformamide (15 mL) was added sodium hydride (1.4 g, 40 mmol, 66% in oil) at 0° C., which was stirred for 20 minutes at room temperature and for 1 hour at 70° C. Water was added to the reaction mixture, 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 NH silica gel column chromatography (ethyl acetate:heptane=1:1) to obtain the title compound (1.9 g, 66%).

後処理

  1. extractionwas then extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. customthe solvent was evaporated under a reduced pressure
  4. customThe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:1)

出典と根拠

ORDレコード
ord-76c644397f444352bb4e0c7420741d8f
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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