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Short Note

Ethyl (E)-2-Methyl-5-phenyl-2-pentenoate

by
Martin J. Stoermer
* and
John T. Pinhey
Division of Organic Chemistry, School of Chemistry F11, The University of Sydney, N.S.W 2006, Australia
*
Author to whom correspondence should be addressed.
*
Current address: Victorian College of Pharmacy, Monash University (Parkville Campus), 381 Royal Parade, Parkville, Victoria 3052, Australia
Molecules 1998, 3(3), M62; https://doi.org/10.3390/M62
Submission received: 27 February 1998 / Published: 6 March 1998
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Versions Notes
Molecules 03 m62 i001
The general part of the experimental section [1] has been presented elsewhere. To a solution of (1-carbethoxyethylidene)triphenylphosphorane (5.76 g, 15.7 mmol) in dry benzene (100 ml) was added 3-phenylpropanal (2 g, 14.9 mmol). The mixture was refluxed for 6 hours and the solvent was removed. The residue was purified by flash chromatography (ethyl acetate/light petroleum 5:95), followed by preparative HPLC (ethyl acetate/light petroleum 1:99) to yield ethyl(E)-3-methyl-5-phenyl-2-pentenoate (2.71 g, 83%) as a colourless oil.
B.p. 130°/0.4 mmHg (Kugelrohr)
Anal. calc. for C14H18O2 (218.29): C 77.0, H 8.3; found: C 77.0, H 7.9.
IR (film) 2983, 2933, 1710 (s, C=O), 1619, 1452, 1364, 1266(s), 1177, 1118(s), 1082, 1029, 741 cm-1.
1H-NMR (400 MHz, CDCl3) 1.28 (3H, t, J 7.1 Hz, -OCH2CH3), 1.79 (3H, dt, J 1.5, 1.0 Hz, CH3), 2.48 (2H, m, CH2), 2.75 (2H, bt, J 7.6 Hz, Ph-CH2), 4.19 (2H, q, J 7.1 Hz, -OCH2CH3), 6.81 (1H, tq, J 7.35, 1.5 Hz, =CH), 7.14-7.35 (5H, m, ArH). Stereochemistry confirmed by n.O.e. difference spectroscopy. Irradiation at 1.79 produced no n.O.e. at 6.81, and irradiation at 6.81 produced no n.O.e. at 1.79.
13C-NMR (15 MHz, CDCl3) 12.27, 14.22 (CH3), 30.52, 34.74, 60.32, (CH2), 126.0, 128.1, 128.2 (CH), 128.4 (quat, C2), 140.8 (=CH), 141.2 (quat, C1'), 168.0 (quat, C1).
EI-MS 218(M+, 12%), 173(5), 91(100).
Acknowledgment: The authors gratefully acknowledge financial support from the Australian Research Council and The University of Sydney.

References and Notes

  1. Moloney, M.G.; Pinhey, J.T.; Stoermer, M.J. "Vinyl Cation Formation by Decomposition of Vinyl-lead Triacetates. The reactions of Vinylmercury and Vinyltin Compounds with Lead Tetraacetate". J. Chem. Soc. Perkin Trans. 1 1990, 10, 2645. [Google Scholar] [CrossRef]
Sample Availability: No sample available.

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MDPI and ACS Style

Stoermer, M.J.; Pinhey, J.T. Ethyl (E)-2-Methyl-5-phenyl-2-pentenoate. Molecules 1998, 3, M62. https://doi.org/10.3390/M62

AMA Style

Stoermer MJ, Pinhey JT. Ethyl (E)-2-Methyl-5-phenyl-2-pentenoate. Molecules. 1998; 3(3):M62. https://doi.org/10.3390/M62

Chicago/Turabian Style

Stoermer, Martin J., and John T. Pinhey. 1998. "Ethyl (E)-2-Methyl-5-phenyl-2-pentenoate" Molecules 3, no. 3: M62. https://doi.org/10.3390/M62

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