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

HRID 1056815

反応式

HRID 1056815 の反応式
[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

参加物

6

反応物 3

HCID 1264-HydroxybenzaldehydeHCID 10796Cesium carbonateHCID 23392Picolyl chloride hydrochloride

生成物 1

HCID 7596674-(Pyridin-2-ylmethoxy)benzaldehyde収率 77%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-aa1cce5f5f384bfcbc6d3037a277e167
出典データセット
uspto-grants-2016_07
特許番号
US09399635B2

関連ノート

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