Dimethylformamide → 2-(4-Bromo-benzyloxy)-5-methyl-pyridine

HRID 640184

反応式

HRID 640184 の反応式
CN(C)C=O.[Br:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11][OH:12])=[CH:9][CH:8]=1.[H-].[Na+].F[C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][N:19]=1>O>[Br:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11][O:12][C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][N:19]=2)=[CH:9][CH:8]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 701194-Bromobenzyl alcoholHCID 27746352-Fluoro-5-methylpyridine

生成物 1

HCID 592554492-(4-Bromo-benzyloxy)-5-methyl-pyridine収率 59.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To an N,N-dimethylformamide (50.0 mL) solution of 4-bromobenzyl alcohol (4.54 g, 24.3 mmol) was added sodium hydride (1.00 g, 25.0 mmol, 60% in oil) under nitrogen atmosphere at 0° C., which was stirred for 30 minutes at room temperature. 2-Fluoro-5-methylpyridine (1.80 g, 16.2 mmol) was then added at 0° C., and stirred for 5 hours at room temperature. Water was added to the reaction solution at room temperature, which was then extracted with ethyl acetate. The organic layer was separated and 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=1:15) to obtain the title compound (2.67 g, 59.3%).

後処理

  1. stirringstirred for 5 hours at room temperature
  2. extractionwhich was then extracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with saturated aqueous sodium chloride
  5. customthe solvent was evaporated under a reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:15)

出典と根拠

ORDレコード
ord-b89839065a5845a1a6b41ef1a323e8f5
出典データセット
uspto-grants-2010_04
特許番号
US07691882B2

関連ノート

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