Dimethylformamide → 5-(Benzyloxy)-2-methylpyridine

HRID 78115

반응식

HRID 78115 반응식
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

참가 물질

6

반응물 4

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

생성물 1

HCID 123972515-(Benzyloxy)-2-methylpyridine수율 66%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
0 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-9e7c603bc87544609aed79f158418130
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841327B2

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