Water → 6-(Benzyloxy)nicotinaldehyde

HRID 78285노트

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HRID 78285 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](Br)=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.CN(C)[CH:23]=[O:24].O>C(OCC)C.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[N:10]=[CH:11][C:12]([CH:23]=[O:24])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 6228DimethylformamideHCID 111081912-Benzyloxy-5-bromopyridineHCID 178418339Butyllithium

생성물 1

HCID 211022056-(Benzyloxy)nicotinaldehyde수율 86%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8857Ethyl Acetate용매

반응 조건

온도
-78 °C

실험 절차

To a solution of 2-benzyloxy-5-bromopyridine described in Manufacturing Example 231-1-1 (53.0 g, 201 mmol) in diethyl ether (500 mL) was added n-butyl lithium (82.8 mL, 2.67 M n-hexane solution, 221 mmol) was added dropwise on a dry ice-ethanol bath (−78° C.) under nitrogen atmosphere, which was stirred for 30 minutes at −78° C. While cooling at the same temperature, N,N-dimethylformamide (17.6 g, 241 mmol) was added to this reaction mixture, which was stirred for 30 minutes. Water and ethyl acetate were added to the reaction mixture, which was stirred for 10 minutes at room temperature, the organic layer was then separated. The organic layer was washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:5 then 1:4) to obtain the title compound (36.8 g, 86%).

후처리

  1. additionwas added dropwise on a dry ice-ethanol bath (−78° C.) under nitrogen atmosphere
  2. additionwas added to this reaction mixture, which
  3. stirringwas stirred for 30 minutes
  4. stirringwas stirred for 10 minutes at room temperature
  5. customthe organic layer was then separated
  6. washThe organic layer was washed with water and saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under a reduced pressure
  10. customThe residue was purified by NH silica gel column chromatography (ethyl acetate

출처 및 근거

ORD 기록
ord-dbcf44c5a86945a79cc1177e056220af
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841327B2

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