3-氰基吡啶 → (4,5-Dimethylfuran-2-yl)-(3-pyridyl)-methanone

HRID 228814

反应方程式

HRID 228814 反应方程式
[CH3:1][C:2]1[O:3][CH:4]=[CH:5][C:6]=1[CH3:7].C([Li])CCC.[C:13]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)#N.Cl.C([O:24]CC)C>CCCCCC>[CH3:7][C:6]1[CH:5]=[C:4]([C:13]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[O:24])[O:3][C:2]=1[CH3:1]

参与物

7

反应物 5

HCID 793-氰基吡啶HCID 313海萝胶HCID 3283乙醚2 次HCID 343372,3-二甲基呋喃HCID 178418339正丁基锂

产物 1

HCID 23078492(4,5-Dimethylfuran-2-yl)-(3-pyridyl)-methanone收率 18%

试剂、催化剂与溶剂 1

HCID 8058正己烷溶剂

反应条件

温度
0 °C

实验过程

2,3-Dimethylfuran (5 g) was dissolved in diethyl ether (75 ml) under an argon atmosphere, a 1.6 M hexane solution (35.7 ml) of n-butyllithium was added dropwise thereto at 0° C., and the mixture was stirred under reflux for 2.5 hr. Thereafter, the reaction solution was cooled to −78° C., a solution of 3-cyanopyridine (6.0 g) in diethyl ether (20 ml) was added dropwise thereto, and the mixture was stirred at room temperature for 3 hr. The reaction solution was poured into ice to stop the reaction solution. The reaction solution was adjusted to pH 5 by the addition of 2 M hydrochloric acid and was extracted with chloroform. The chloroform layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using hexane-ethyl acetate to give (4,5-dimethylfuran-2-yl)-(3-pyridyl)-methanone (1.9 g, yield 18%).

后处理

  1. temperatureunder reflux for 2.5 hr
  2. temperatureThereafter, the reaction solution was cooled to −78° C.
  3. stirringthe mixture was stirred at room temperature for 3 hr
  4. additionThe reaction solution was poured into ice
  5. extractionwas extracted with chloroform
  6. washThe chloroform layer was then washed with water
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. customThe solvent was removed by distillation under the reduced pressure
  9. customthe residue was purified by column chromatography

来源与证据

ORD记录
ord-00de61681a0b4b3ea3b18142c91a55d7
来源数据集
uspto-grants-2009_07
专利号
US07560558B2

关联笔记

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