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化学学报
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化学学报 ›› 2009, Vol. 67 ›› Issue (11): 1237-1242. 上一篇    下一篇

研究论文

含醛基功能化离子液体为载体液相合成氨基醚类化合物

易封萍*,a 孙海洋a,b 潘仙华a

  

  1. (a上海应用技术学院香料香精技术与工程学院 上海 200235)
    (b上海海洋大学食品学院 上海 201306)

  • 投稿日期:2008-05-28 修回日期:2008-07-20 发布日期:2009-06-14
  • 通讯作者: 易封萍

Solution Phase Parallel Synthesis of Amino-ether Compounds Using Aldehyde-Functionalized Ionic Liquid as Support

Yi, Fengping *,a Sun, Haiyang a,b Pan, Xianhua a   

  1. (a School of Perfume and Aroma Technology, Shanghai Institute of Technology, Shanghai 200235)
    (b College of Food Science & Technology, Shanghai Ocean University, Shanghai 201306)
  • Received:2008-05-28 Revised:2008-07-20 Published:2009-06-14
  • Contact: Yi, Fengping

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1685

被引次数

11 | 1

以1-甲基咪唑、对二氯苄、对羟基苯甲醛和四氟硼酸钠为原料, 制备了一种含醛基的新型功能化离子液体1-(4-对甲酰基苯氧基亚甲基苄基)-3-甲基咪唑四氟硼酸盐(简写为[fmmim][BF4]). 为拓展功能化离子液体为载体的液相合成反应体系, 以该含醛基功能化离子液体为可溶性液相载体, 进行了Williamson醚化的合成反应, 较高产率和纯度得到了一系列氨基醚类化合物, 切割后得到的目标化合物不需要进行进一步的柱色谱纯化处理, 产率为81%～85%, 纯度为96%～99%. 回收得到的功能化离子液体可以重复套用多次而不影响其功效, 目标化合物的产率在81%～84%之间波动. 结果表明该方法可高效率地用于基于Williamson醚化反应的液相组合化学合成.

关键词: 功能化离子液体, 载体, 氨基醚, 液相合成, 组合化学

The facile and new type aldehyde functionalized ionic liquid 1-[4-(p-formylphenoxy methylene) benzyl]-3-methylimidazolium tetrafluoroborate (abbreviated as [fmmim][BF4]) was prepared via 1-methyl- imidazole, p-xylylene dichloride, p-hydroxybenzaldehyde and sodium tetrafluoroborate as raw materials. In order to develop the use of functionalized ionic liquids in solution phase parallel synthesis, amino-ether compounds were prepared via Williamson etherification using the aldehyde-functionalized ionic liquid as soluble support. The target compounds were obtained in good yields and high purities without column chromatographic purification after cleavage. The yields were 81%～85%, and the purities were 96%～99%. The recovered functionalized ionic liquid could be reused for several times without affecting its activity, and the yields of desired compound was fluctuated between 81%～84%. These results indicated that the presented method could be applied efficiently to the solution-phase combinatorial chemistry based on Williamson etherification.

Key words: functionalized ionic liquid, support, amino-ethers, solution phase synthesis, combinatorial chemistry