Dimethylformamide → 5-(Benzyloxy)-2-methylpyridine

HRID 78115

反応式

HRID 78115 の反応式
CN(C)C=O.[OH:6][C:7]1[CH:8]=[N:9][C:10]([CH3:13])=[CH:11][CH:12]=1.[H-].[Na+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O>[CH2:16]([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[N:9][CH:8]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 142752-Methyl-5-hydroxypyridineHCID 24758Sodium hydride

生成物 1

HCID 123972515-(Benzyloxy)-2-methylpyridine収率 66%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

To an N,N-dimethylformamide (50 mL) solution of 3-hydroxy-6-methylpyridine (5.00 g, 45.8 mmol) was added sodium hydride (2.02 g, 50.4 mmol, 60% in oil), which was stirred for 15 minutes at 0° C. Next, benzyl bromide (5.99 mL, 50.4 mmol) was added to this reaction mixture at 0° C., which was stirred for 3.5 hours at room temperature. Water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (heptane: ethyl acetate=2:1) to obtain the title compound (5.99 g, 66%).

後処理

  1. stirringwhich was stirred for 3.5 hours at room temperature
  2. extractionwas extracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with water and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under a reduced pressure
  8. customThe residue was purified by silica gel column chromatography (heptane: ethyl acetate=2:1)

出典と根拠

ORDレコード
ord-9e7c603bc87544609aed79f158418130
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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