Wittig Reaction; Ethyl 3-(1-pyrenyl)acrylate
SyntheticPage 506
DOI:
10.1039/SP506
Submitted Sep 14, 2011, published Sep 14, 2011
Anish Mistry (
a.mistry@warwick.ac.uk)
A contribution from
Fox Group, Warwick University
Chemicals Used
Ethyl (triphenylphosphoranyliden)acetate (1 equiv, prepared)
1-pyrenecarboxaldehyde (1 equiv, purchased from Sigma-Aldrich)
Toluene
Chloroform
Petroleum ether (40 - 60 oC)
Procedure
1-pyrenecarboxaldehyde (1.13 g, 4.9 mmol) was added to a solution of ethyl (triphenylphosphoranyliden)acetate (1.71 g, 4.9 mmol) in toluene (80 ml) and the reaction mixture heated under reflux for approximately 96 hours. The mixture was left to cool and solvent removed in vacuo to form a crude yellow/orange solid. The crude product was purified by coloumn chromatography using (8:2) chloroform : petroleum ether (40 - 60 oC) to yield yellow granules (1.3 g, 89%).
Author's Comments
Data
δH(400MHz, CDCl3) ppm: 1.42 (3H, t, J 7.0, CH3), 4.37 (2H, q, J 7.0, CH2), 6.71 (1H, d, J 15.5, CH alkene), 8.00 - 8.29 (8H, m, aryl), 8.49 (1H, d, J 9.5, aryl), 8.83 (1H, d, J 15.5, CH alkene)
Lead Reference
Ta-Hsien Chuang, Shiow-Ju Lee, Cheng-Wei Yang and Pei-Lin Wu, Expedient synthesis and structure–activity relationships of phenanthroindolizidine and phenanthroquinolizidine alkaloids,
Org. Biomol. Chem., 2006, 4, 860–867
http://dx.doi.org/10.1039/b516152e
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Keywords: aldehydes, alkenes, aromatics/arenes, phosphorus ylide, Wittig
