A one-pot synthesis of unsymmetrical bis-styrylbenzenes

Tetrahedron Letters

Volumn 50, Issue 46, 2009, Pages 6228-6230

  Flaherty, Daniel P ^a   Dong, Yuxiang ^a   Vennerstrom, Jonathan L ^a  

^a NEBRASKA MEDICAL CENTER   (United States)

Author keywords

Alzheimer's disease; Bis styrylbenzenes; Heck reaction; Horner Wadsworth Emmons reaction

Indexed keywords

BENZENE DERIVATIVE; BISTYRYLBENZENE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; HECK REACTION; HORNER WADSWORTH EMMONS REACTION; ONE POT SYNTHESIS;

EID: 70349478610     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.08.083     Document Type: Article

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16. 2O and ether to yield (E,E)-1-styryl-4-(4-cyanostyryl)benzene (4a) (0.17 g, 84%).
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18. Several attempts to synthesize 4h with 1.1 mol equiv of 3d using the one-pot procedure resulted in low yields of the desired product and recovery of the (E)-(4-methoxycarbonylstyrylbenzyl) phosphonate starting material. The lower reactivity of 3d may be due to its less electrophilic carbonyl carbon.
19. 2O (15 mL) and filtered to yield (E,E)-1-styryl-4-(4-cyanostyryl)benzene (4a) (0.086 g, 82%).
20. Using a HWE reaction, we were able to isolate 5c in 90% yield using sodium methoxide at 80 °C compared to a previously reported (Kung, H. F.; Lee, C.-W.; Zhuang, Z.-P.; Kung, M.-P.; Hou, C.; Plssl, K. J. Amer. Chem. Soc. 2001, 123, 12740.) 30% yield using sodium hydride at room temperature.