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Ethyl (Z)-3-Methyl-5-phenyl-2-pentenoate.doc

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Ethyl (Z)-3-Methyl-5-phenyl-2-pentenoate

Ethyl (Z)-3-methyl-5-phenyl-2-pentenoate /molbank/m0052.htm Molecules 1998, 3, M52 Ethyl (Z)3Methyl5phenyl2pentenoate Martin J. Stoermer* and John T. Pinhey Division of Organic Chemistry, School of Chemistry F11, The University of Sydney, N.S.W 2006, Australia. *Current address: Victorian College of Pharmacy, Monash University (Parkville Campus), 381 Royal Parade, Parkville, Victoria 3052, Australia. Phone: +61 3 990 39000, Fax: +61 3 e-mail: martin.stoermer@.au, .au/martin/ Received: 27 February 1998 / Published: 6 March 1998 The synthetic procedure [1] has been presented elsewhere. Ethyl (Z)-3-methyl-5-phenyl-2-pentenoate was obtained (2.23 g, 23%) as a colourless oil. B.p. 105°/0.5 mmHg (Kugelrohr) Anal. calc. for C14H18O2 (218.29): C 77.0, H 8.3; found: C 76.9, H 8.1. UV (ethanol) 310 (289), 210 (16220) nm. IR (film) 1713 (s, C=O), 1650, 1229, 1165.1053 cm-1 1H-NMR (400 MHz, CDCl3) 1.28 (3H, t, J 7.2 Hz, -OCH2CH3), 1.88 (3H, d, J 1.5 Hz, CH3), 2.78 (2H, bt, J 8.0 Hz, Ph-CH2), 2.92 (2H, m, CH2), 4.14 (2H, q, J 7.2 Hz, -OCH2CH3), 5.69 (1H, tq, J 1.1, 1.5 Hz, =CH), 7.16-7.32 (5H, m, ArH). Stereochemistry confirmed by n.O.e. difference spectroscopy. Irradiation at 1.88 produced a 6% n.O.e. at 5.69 (also 1% at 2.92, 1% at 2.78). Irradiation at 5.69 produced an 8% n.O.e. at 1.88. 13C-NMR (15 MHz, CDCl3) 14.15, 25.06 (CH3), 34.41, 35.32, 59.15, (CH2), 116.6 (=CH); 125.7, 128.1, 128.1 (CH), 141.5 (quat, C1), 158.8 (quat, C3), 165.8 (quat, C1). EI-MS 218 (M+, 18%), 173(22), 172(12), 145(17), 144(28), 129(!3), 92(13), 91(100), 65(14). Acknowledgment: The authors gratefully acknowledge financial support from the Australian Research Council and The University of Sydney. References and otes 1. Preceding article. 1 von 2 06.05.2009 11:44 Ethyl (Z)-3-methyl-5-phenyl-2-pentenoate /molbank/m0052.htm Sample Availability: No sample available. ? 1998 MDPI. All rights reserved 2 von 2 06.05.2009 11:44