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Short Note

Ethyl (Z)-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), M63; https://doi.org/10.3390/M63
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 m63 i001
The synthetic procedure [1] has been presented elsewhere. Ethyl (Z)-2-methyl-5-phenyl-2-pentenoate (0.24 g, 7%) was prepared 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 77.4, H 8.2.
IR (film) 2961, 2928, 1701 (s, C=O), 1456, 1240, 1216, 1184(s), 1124(s), 1030 69(s) cm-1.
1H-NMR (400 MHz, CDCl3) 1.29 (3H, t, J 7.1 Hz, -OCH2CH3), 1.88 (3H, dt, J 1.5, 1.2 Hz, CH3), 2.68-2.82 (4H, m, 2xCH2), 4.18 (2H, q, J 7.1 Hz, -OCH2CH3), 5.95 (1H, tq, J 7.10, 1.5 Hz, =CH), 7.14-7.32 (5H, m, ArH). Stereochemistry confirmed by n.O.e. difference spectroscopy. Irradiation at 1.88 produced a 16% n.O.e. at 5.95 and irradiation at 5.95 produced a 10% n.O.e. at 1.88.
13C-NMR (15 MHz, CDCl3) 14.02, 20.06 (CH3), 30.84, 35.32, 59.67, (CH2), 125.6 (CH), 17.7 (quat, C2), 128.0 (2xCH), 141.0 (=CH); 141.3 (quat, C1'), 167.5 (quat, C1).
EI-MS 218(M+, 45%), 173(23), 172(15), 144(10), 92(23), 91(100), 65(16).
Acknowledgment: The authors gratefully acknowledge financial support from the Australian Research Council and The University of Sydney.

References and Notes

  1. Preceding article.
Sample Availability: No sample available.

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MDPI and ACS Style

Stoermer, M.J.; Pinhey, J.T. Ethyl (Z)-2-Methyl-5-phenyl-2-pentenoate. Molecules 1998, 3, M63. https://doi.org/10.3390/M63

AMA Style

Stoermer MJ, Pinhey JT. Ethyl (Z)-2-Methyl-5-phenyl-2-pentenoate. Molecules. 1998; 3(3):M63. https://doi.org/10.3390/M63

Chicago/Turabian Style

Stoermer, Martin J., and John T. Pinhey. 1998. "Ethyl (Z)-2-Methyl-5-phenyl-2-pentenoate" Molecules 3, no. 3: M63. https://doi.org/10.3390/M63

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