Chin. J. Org. Chem. ›› 2003, Vol. 23 ›› Issue (7): 682-685. Previous Articles     Next Articles

2,2'-联吡啶桥连的双-4,4'-联吡啶哑铃型化合物的合成

许新华;卢锐亮;黄荣新;张秋林;陈雄   

  1. 湖南大学化学化工学院
  • 发布日期:2003-07-25

Synthesis of Dumbell-Shaped Compound of Bis-4,4'-bipyridinie Bridged by 2,2'-Bipyridine

Xu Xinhua;Lu Ruiliang;Huang Rongxin;Zhang Qiulin;Chen Xiong   

  1. College of Chemistry and Chemical Engineering, Hunan University
  • Published:2003-07-25

The reaction of di(ethylene glycol) with p-toluenesulfonate chloride in CH2C12 at 0 °C ~ r. t. in the presence of Et3N gave tosylate of 2-(hydroxyethoxy) ethanol (3) in 88% yield. Condensation of 3 with A-tert-butylbenzoyl chloride in CH2C12 at room temperature in the presence of pyridine afforded tosylate of 2-(p-tert- butylbenzoyloxyethoxy)ethanol (4) in 96% yield. Substitution of 4 with 4-hydroxybenzylmethanol in CH3CN and in the presence of CsF/K2CO3 at 70 °C gave 2-(j3-tert-butylbenzoyloxyethoxy)ethoxyben2ylic alcohol (5) in 98% yield. Bromination of 5 using NBS and PPh3 in THF at room temperature resulted in the formation of 2-( p-tert- butylbenzoyloxyethoxy)ethoxybenzylic bromide (6) in 95% yield. The reaction of 6 with 4,4'-bipyridine in CH3CN at 60 °C gave iV-2-(p- tert-butylbenzoyloxyethoxy) ethoxybenzyl-4, 4'-bipyridinium hexafluorophosphate (7) in 85% yield, which reacted with a, a'-bis (bromomethyl)-2,2'-bipyridine in CH3CN at 60 T! for 36 h to obtain the title compounds in 45% yield.

Key words: BIPYRIDINE;CROWN ETHER COMPOUNDS;PHOSPHATE;GLYCEROL;ACYL CHLORIDES P, ACETONITRILE

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