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Hydrolysis of Ethyl 3-(1-pyrenyl)propanoate; 3-(1-Pyrenyl)propionic acid

SyntheticPage 513
DOI: 10.1039/SP513
Submitted Oct 06, 2011, published Oct 11, 2011
Anish Mistry (a.mistry@warwick.ac.uk)
A contribution from Fox Group, Warwick University


			Reaction Scheme: <img src="/images/empty.gif" alt="" />Hydrolysis of <span id="csm1321807999359" class="csm-chemical-name" title="Ethyl 3-(1-pyrenyl)propanoate">Ethyl 3-(1-pyrenyl)propanoate</span><img src="/images/empty.gif" alt="" />

Chemicals Used

Ethyl 3-(1-pyrenyl)propanoate (1 equiv, prepared)
KOH (2 equiv, Fischer Scientific)
Ethanol
pH2 buffer solution (prepared)

Procedure

Under a dinitrogen atmosphere, ethyl 3-(1-pyrenyl)propanoate (0.5 g, 1.6 mmol) was dissolved in warm ethanol (10 ml), then water (1 ml) and solid potassium hydroxide (0.18 g, 3.2 mmol) was added and the solution left stirring overnight. The reaction mixture was cooled and solvent removed under vacuo. Buffer solution (pH 2, 10 ml) was added and the mixture was extracted with ethyl acetate (10 ml x 3). The combined organics were dried over Na2SO4 and solvent was removed in vacuo to yield orange crystalline solid (0.45 g, 99%)

Author's Comments

The reaction most probably takes less time (a couple of hours or so) however I just left it overnight to be sure.

Data

δH(400MHz, CDCl3) ppm: 2.94 (2H, t, J 8, CH2), 3.72 (2H, t, J 8, CH2), 7.92 (1H, d, J 8, aryl), 7.99 - 8.21 (7H, m, aryl), 8.28 (1H, d, J 9, aryl).





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

Other References

(1-Pyrenylmethyl)amino alcohols, a new class of antitumor DNA intercalators. Discovery and initial amine side chain structure-activity studies, Kenneth W. Bair, Richard L. Tuttle, Vincent C. Knick, Micheal Cory and David D. McKee, Journal of Medicinal Chemistry, 1990, 33(9), 2385-93.

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

Keywords: esters, hydrolysis

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