Molecules 1998, 3, M72

Ethyl (Z)-3-(2-Methoxyphenyl)-2-butenoate

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 99039582, e-mail: [email protected], http://synapse.vcp.monash.edu.au/martin/

Received: 27 February 1998 / Published: 6 March 1998

The synthetic procedure [1] has been presented elsewhere. Ethyl (Z)-3-(2-methoxyphenyl)-2-butenoate was obtained (1.63 g, 17%) as a colourless oil.

B.p. 159°/12 mmHg (Kugelrohr) (lit.[2] (E) and (Z)-mixture, 162-4°/16 mmHg

UV (ethanol) 272 (2982), 212 (19925) nm.

IR (film) 2985, 1723 (s, C=O), 1646, 1600, 1485, 1454, 1438, 1369, 1262, 1238(s), 1154(s), 1115, 1046(s), 738(s) cm^-1.

¹H-NMR (400 MHz, CDCl₃) 1.05 (3H, t, J 7.3 Hz, -OCH₂CH₃), 2.14 (3H, d, J 1.5 Hz, CH₃), 3.79 (3H, s, OCH₃), 3.96 (2H, q, J 7.3 Hz, -OCH₂CH₃), 5.95 (1H, q, J 1.5 Hz, =CH), 6.89 (1H, bd, J 8.2 Hz, H3'), 6.92 (1H, ddd, J 7.5, 7.2, 1.0 Hz, H5'), 7.01 (1H, dd, J 7.5, 1.9 Hz, H6'), 7.29 (1H, ddd, J 8.2, 7.2, 1.9 Hz, H4'). Stereochemistry confirmed by n.O.e. difference spectroscopy. Irradiation at 2.14 produced a 4% n.O.e. at 5.95. Irradiation at 5.95 produced a 6% n.O.e. at 2.14.

¹³C-NMR (100 MHz, CDCl₃) 13.91, 26.03, 55.49 (CH₃), 59.46, (CH₂), 110.7 (=CH); 116.9, 120.3, 128.0, 128.7 (CH), 130.4 (quat, C1'), 153.1, 155.4 (quat), 165.6 (quat, C1).

EI-MS 221(M⁺+1, 16%), 220 (M⁺, 94), 190 (40), 189 (100), 176 (20), 175 (100), 162 (37), 161 (98), 159 (76), 147 (31), 146 (16), 145 (46), 135 (20), 133 (68), 131 (100), 115 (61), 104 (21), 103 (55), 102 (19), 91 (90), 89 (33), 78 (35), 77 (77).

Acknowledgment: The authors gratefully acknowledge financial support from the Australian Research Council and The University of Sydney.

1. Preceding article.
2. Scmitt, J. Suquet, M.; Comoy, P.; Boitard, J.; Callet, G.; Clim, T.; Le Meur, J. Bull. Soc. Chim. Fr. 1966, 3, 953.

Sample Availability: No sample available.

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