2-Vinylpyridine → 2-(m-Nitrostyryl)pyridine

HRID 2086784ノート

反応式

HRID 2086784 の反応式
I[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=1.[CH:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)=[CH2:12].C(=O)(O)[O-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N+:8]([C:4]1[CH:3]=[C:2](/[CH:12]=[CH:11]/[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[CH:7]=[CH:6][CH:5]=1)([O-:10])=[O:9]

参加物

7

反応物 3

HCID 75212-VinylpyridineHCID 125741-Iodo-3-nitrobenzeneHCID 516892Sodium Bicarbonate2 回

生成物 1

HCID 53764932-(m-Nitrostyryl)pyridine収率 49.7%

試薬・触媒・溶媒 3

HCID 70681Tetrabutylammonium Chloride触媒HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

A mixture of 1-iodo-3-nitrobenzene (7.47 g), 2-vinylpyridine (4.73 g), palladium(II) acetate (0.20 g), tetrabutylammonium chloride (8.34 g) and sodium bicarbonate (6.3 g) in N,N-dimethylformamide (50 ml) was stirred at 110° C. for 5 hours. Then the mixture was poured into aqueous sodium bicarbonate and extracted with ethyl acetate twice. The combined organic phase was washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated. The resultant solid was collected and washed with isopropyl ether to give 2-[(E)-2-(3-nitrophenyl)vinyl]pyridine (3.37 g).

後処理

  1. extractionextracted with ethyl acetate twice
  2. washThe combined organic phase was washed with aqueous sodium bicarbonate and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe resultant solid was collected
  6. washwashed with isopropyl ether

出典と根拠

ORDレコード
ord-c75ae2c3dc50444ba26c94e2ca183824
出典データセット
uspto-grants-2004_04
特許番号
US06727245B2

反応ノート

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