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Short Note

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

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), M72; https://doi.org/10.3390/M72
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 m72 i001
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.

References and Notes

  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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MDPI and ACS Style

Stoermer, M.J.; Pinhey, J.T. Ethyl (Z)-3-(2-Methoxyphenyl)-2-butenoate. Molecules 1998, 3, M72. https://doi.org/10.3390/M72

AMA Style

Stoermer MJ, Pinhey JT. Ethyl (Z)-3-(2-Methoxyphenyl)-2-butenoate. Molecules. 1998; 3(3):M72. https://doi.org/10.3390/M72

Chicago/Turabian Style

Stoermer, Martin J., and John T. Pinhey. 1998. "Ethyl (Z)-3-(2-Methoxyphenyl)-2-butenoate" Molecules 3, no. 3: M72. https://doi.org/10.3390/M72

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