Print version Print setup

Knoevenagel reaction; the of α,β-unsaturated ketone (1E,5E)-1,6-Di(furan-2-yl)hexa-1,5-diene-3,4-dione

SyntheticPage 508
DOI: 10.1039/SP508
Submitted Sep 27, 2011, published Sep 28, 2011
Jérôme Husson (jerome.husson@univ-fcomte.fr)
A contribution from Institut UTINAM


			Reaction Scheme: <IMG src="/images/empty.gif"><IMG alt="" src="/images/empty.gif">Knoevenagel reaction<IMG alt="" src="/images/empty.gif"><IMG src="/images/empty.gif">

Chemicals Used

Furfuraldehyde (ACROS)

piperidine (ACROS)

2,3-butanedione (Sigma-Aldrich)

Absolute ethanol (VWR)

Procedure

In an Erlenmeyer flask fitted with a stopper, are successively placed furfuraldehyde (21.5 mL; 259.5 mmol), ethanol (20 mL), 2,3-butanedione (11,4 mL; 130.4 mmol) and 4 drops of piperidine. The resulting mixture is stirred at room temperature for 7 d protected from light. The resulting orange precipitate is filtered, washed with cold ethanol until washings are clear and dried under vacuum over P2O5. Yield: 1.96 g (6.2%).

Author's Comments

Furfuraldehyde must be distilled prior to use. The reaction is easy to perform despite long reaction time and limited yield. Compound so obtained was sufficiently pure to be used without purification.

Data

Mp= 160°C

1H NMR (300 MHz, CDCl3) ppm = 7.61 (2H, d, J= 15.8 Hz), 7.57 (2H, d, J= 1.5 Hz), 7.30 (2H, d, J= 15.8 Hz), 6.80 (2H, d, J= 3.3 Hz), 6.53 (2H, dd, J= 1.5 Hz, J= 3.3 Hz).

Lead Reference

Constable, E.C. et al. Dalton Trans., 2009, 6634.

Other References

Hernandez Redondo, A. Ph. D. Thesis, Basel University (Switzerland), 2009. Available online at http://edoc.unibas.ch/994/1/Dissertation_Ana_Hernandez.pdf (accessed 27/09/2011).

This page has been viewed approximately 4832 times since records began.

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

Keywords: alkenes, heterocyclic compounds, ketones

Post new comment
Loading ...