Print version Print setup

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


			Reaction Scheme: <img src="/images/empty.gif" alt="" /><img src="/images/empty.gif" alt="" /><img src="/images/empty.gif" alt="" />Wittig Reaction<img src="/images/empty.gif" alt="" /><img src="/images/empty.gif" alt="" /><img src="/images/empty.gif" alt="" />

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

This page has been viewed approximately 7853 times since records began.

Get structure file (.cdx, .sk2, .mol)

Keywords: aldehydes, alkenes, aromatics/arenes, phosphorus ylide, Wittig

Post new comment
Loading ...