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

HRID 77901

반응식

HRID 77901 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-facb86b0ae294aae8f86b7ad66b231a8
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841327B2

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