4-Hydroxybenzaldehyde → 4-(Pyridin-2-ylmethoxy)benzaldehyde

HRID 1056815

반응식

HRID 1056815 반응식
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl.Cl[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1>CN(C)C=O.C(OCC)(=O)C>[N:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 1264-HydroxybenzaldehydeHCID 10796Cesium carbonateHCID 23392Picolyl chloride hydrochloride

생성물 1

HCID 7596674-(Pyridin-2-ylmethoxy)benzaldehyde수율 77%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
50 °C

실험 절차

In 5.0 mL of N,N-dimethylformamide was dissolved 611 mg (5.00 mmol) of 4-hydroxybenzaldehyde. To this solution were added 3.26 g (10.0 mol) of cesium carbonate and 0.98 g (6.0 mmol) of 2-chloromethylpyridine hydrochloride at room temperature and the mixture was stirred at 50° C. overnight. The resulting reaction mixture was diluted with ethyl acetate (100 mL), washed with water and then with saturated brine (each in an amount of 30 mL), and dried over magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20 to 50/50) to give 821 mg (77% yield) of the title compound as a light green crystal.

후처리

  1. customThe resulting reaction mixture
  2. washwashed with water
  3. dry with materialwith saturated brine (each in an amount of 30 mL), and dried over magnesium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20 to 50/50)

출처 및 근거

ORD 기록
ord-aa1cce5f5f384bfcbc6d3037a277e167
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09399635B2

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