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Hydrogenation of Ethyl 3-(1-pyrenyl)acrylate; Ethyl 3-(1-pyrenyl)propanoate

SyntheticPage 510
DOI: 10.1039/SP510
Submitted Sep 29, 2011, published Oct 06, 2011
Anish Mistry (a.mistry@warwick.ac.uk)
A contribution from Fox Group, Warwick University
Reaction Scheme: <img src="/images/empty.gif" alt="" />Hydrogenation of <img src="/images/empty.gif" alt="" /><img src="/images/empty.gif" alt="" /><span id="csm1320750042705" class="csm-chemical-name" title="Ethyl 3-(1-pyrenyl)acrylate">Ethyl 3-(1-pyrenyl)acrylate</span><img src="/images/empty.gif" alt="" />

Chemicals Used

Ethyl 3-(1-pyrenyl)acrylate (1 equiv, prepared)
10% Pd/C (2 mol%, Alfa Aeser)
Ethanol
Ethyl Acetate
Hydrogen gas

Procedure

Ethyl 3-(1-pyrenyl)acrylate (3.02 g, 10.1 mmol) was firstly dissolved in ethyl acetate (70 ml). Ethanol (70 ml) and the 10% Pd/C (2 mol%) were then added to the mixture and the air evacuated out the system and replaced with hydrogen. The reaction was left to stir under a hydrogen baloon at room temperature for 29 hours. The reaction mixture was then filtered through a pad of celite with ethyl acetate and the solvent removed under vacuo to yield a dark yellow solid (3.02 g, 99%).

Author's Comments

The main problem if dissolving the Ethyl 3-(1-pyrenyl)acrylate with ethanol hence it was dissolved in ethyl acetate first.
Usually 10 mol% of 10% Pd/C is used which in this reaction full conversion took around two and a half hours, however 10 mol% is a lot of catalyst therfore 2 mol% was used due to lower catalyst loading with a good reaction time.

Data

δH(400MHz, CDCl3) ppm: 1.25 (3H, t, J 7, -O-CH2-CH3), 2.86 (2H, t, J 8, CH2), 3.70 (2H, t, J 8, CH2), 4.17 (2H, q, J 7, -O-CH2-CH3), 7.91 (1H, d, J 8, aryl), 7.97 - 8.20 (7H, m, aryl), 8.28 (1H, d, J 9, aryl).

Lead Reference

Troy Voelker, Haiji Xia, Keith Fandrick, Robert Johnson, Aaron Janowsky, John R. Cashman, 2,5-Disubstituted tetrahydrofurans as selective serotonin re-uptake inhibitors, Bioorganic & Medicinal Chemistry, 2009, 17, 2047–2068.

 

Other References

A. Srikrishna, G. Satyanarayana & Uday V. Desai, Efficient Approach to 4‐Benzyl‐5,5‐dimethyldihydrofuranones: Total Synthesis of (±_bold;)‐Solafuranone, Synthetic Communications, 2007, 37:6, 965-976.

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Keywords: aromatics/arenes, esters, hydrogenation