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6.97 (1H, d, J¼16.1 Hz, CH]CH), 6.92 (2H, d, J¼8.7 Hz, C(6)H), 3.84
J¼16.4 Hz, CH]CH), 2.68 (2H, q, J¼7.5 Hz, CH2), 1.16 (3H, t, J¼7.5 Hz,
(3H, s, C(6)OCH3), 2.38 (3H, s, C(6)CH3).27
CH3).38
4.3.7. (E)-1-Bromo-4-(4-methylstyryl)benzene (3ag). dH (250 MHz,
CDCl3) 7.47 (2H, d, J¼8.6 Hz, C(6)H), 7.40 (2H, d, J¼8.1 Hz, C(6)H),
7.36 (2H, J¼8.6 Hz, C(6)H), 7.18 (2H, d, J¼8.1 Hz, C(6)H), 7.08 (1H, d,
J¼16.2 Hz, CH]CH), 6.97 (1H, d, J¼16.2 Hz, CH]CH), 2.36 (3H, s,
C(6)CH3).28
4.3.20. (E)-1,2-Diphenylethene (3ce). dH (250 MHz, CDCl3) 7.6e7.5
(4H, m, C(6)H), 7.5e7.2 (6H, m, C(6)H), 7.19 (1H, d, J¼17.1 Hz, CH]
CH), 7.11 (1H, d, J¼17.1 Hz, CH]CH).39
4.3.21. (E)-1-Methoxy-4-styrylbenzene (3cf). dH (250 MHz, CDCl3)
7.5e7.2 (7H, m, C(6)H), 7.09 (1H, d, J¼16.4 Hz, CH]CH), 6.99 (1H, d,
J¼16.4 Hz, CH]CH), 6.9e6.8 (2H, m, C(6)H), 3.84 (3 H, s, C(6)OCH3).33
4.3.8. (E)-1-Methyl-4-(3-phenylprop-1-enyl)benzene (3ai). dH (360
MHz, CDCl3) 7.4e7.3 (6H, m, C(6)H), 7.2e7.1 (3H, m, C(6)H), 6.5e6.3
(2H, m, CH]CH), 3.57 (2H, dd, J¼6.8 Hz, J 2.8 Hz, CH2), 2.37 (3H, d,
J¼4.3 Hz, C(6)CH3).29
4.3.22. (E)-Ethyl 3-(4-chlorophenyl)acrylate (3db). dH (250 MHz,
CDCl3) 7.60 (1H, d, J¼16.7 Hz, CH]CH), 7.41 (2H, d, J¼8.5 Hz, C(6)H),
7.31 (2H, d, J¼8.5 Hz, C(6)H), 6.37 (1H, d, J¼16.7 Hz, CH]CH), 4.24
(2H, q, J¼7.1 Hz, CH2), 1.32 (3H, t, J¼7.1 Hz, CH3).40
4.3.9. (E)-4-p-Tolylbut-3-en-2-ol (3aj). dH (250 MHz, CDCl3) 7.30
(2H, d, J¼7.9 Hz, C(6)H), 7.15 (2H, d, J¼7.9 Hz, C(6)H), 6.57 (1H, d,
J¼15.8 Hz, CH]CH), 6.25 (1H, dd, J¼15.8 Hz, 6.5 Hz, CH]CH), 4.51
(1H, dp, J¼6.5 Hz, 1.0 Hz, CH), 2.37 (3H, s, C(6)CH3), 1.93 (1H, w s,
OH), 1.40 (3H, d, J¼6.5 Hz, CH3).30
4.3.23. (E)-tert-Butyl 3-(4-chlorophenyl)acrylate (3dc). dH (250
MHz, CDCl3) 7.50 (1H, d, J¼16.4 Hz, CH]CH), 7.39 (2H, d, J¼8.5 Hz,
C(6)H), 7.29 (2H, d, J¼8.5 Hz, C(6)H), 6.30 (1H, d, J¼16.4 Hz, CH]
CH), 1.51 (9H, s, C(CH3)3).24
4.3.10. (E)-3-(4-Methoxyphenyl)acrylic acid (3ba). dH (360 MHz,
CDCl3) 7.75 (1H, d, J¼15.8 Hz, CH]CH), 7.51 (2H, d, J¼8.3 Hz, C(6)H),
6.92 (2H, d, J¼8.3 Hz, C(6)H), 6.32 (1H, d, J¼15.8 Hz, CH]CH), 3.85
(3H, s, C(6)OCH3).31
4.3.24. (E)-1-(4-Chlorophenyl)pent-1-en-3-one (3dd). dH (360 MHz,
CDCl3) 7.49 (1H, d, J¼16.6 Hz, CH]CH), 7.46 (2H, d, J¼8.2 Hz, C(6)
H), 7.35 (2H, d, J¼8.2 Hz, C(6)H), 6.70 (1H, d, J¼16.6 Hz, CH]CH),
2.66 (2H, q, J¼7.1 Hz, CH2), 1.16 (3H, t, J¼7.1 Hz, CH3).41
4.3.11. (E)-Ethyl 3-(4-methoxyphenyl)acrylate (3bb). dH (250 MHz,
CDCl3) 7.64 (1H, d, J¼15.9 Hz, CH]CH), 7.45 (2H, m, C(6)H), 6.90
(2H, m, C(6)H), 6.30 (1H, d, J¼15.9 Hz, CH]CH), 4.25 (2H, q,
J¼7.3 Hz, CH2), 3.83 (3H, s, C(6)OCH3), 1.33 (3H, t, J¼7.3 Hz, CH3).32
4.3.25. (E)-1-Chloro-4-styrylbenzene (3de). dH (250 MHz, CDCl3)
7.5e7.3 (9H, m, C(6)H), 7.12 (1H, d, J¼16.6 Hz, CH]CH), 7.04 (1H, d,
J¼16.6 Hz, CH]CH).42
4.3.12. (E)-tert-Butyl 3-(4-methoxyphenyl)acrylate (3bc). dH (250
MHz, CDCl3) 7.53 (1H, d, J¼16.1 Hz, CH]CH), 7.44 (2H, d, J¼9.2 Hz,
C(6)H), 6.87 (2H, d, J¼9.2 Hz, C(6)H), 6.23 (1H, d, J¼16.1 Hz, CH]
CH), 3.81 (3H, s, C(6)OCH3), 1.52 (9H, s, C(CH3)3).24
4.3.26. (E)-1-Chloro-4-(4-methoxystyryl)benzene (3df). dH (250
MHz, CDCl3) 7.5e7.4 (4H, m, C(6)H), 7.3 (2H, m, C(6)H), 7.04 (1H, d,
J¼16.2 Hz, CH]CH), 6.9e6.8 (3H, m, CH]CH, C(6)H), 3.83 (3H, s,
C(6)OCH3).43
4.3.13. (E)-1-(4-Methoxyphenyl)pent-1-en-3-one (3bd). dH (250
MHz, CDCl3) 7.48 (1H, d, J¼16.3 Hz, CH]CH), 7.45 (2H, d, J¼9.1 Hz,
C(6)H), 6.87 (2H, d, J¼9.1 Hz, C(6)H), 6.59 (1H, d, J¼16.3 Hz, CH]
CH), 3.79 (3H, s, C(6)OCH3), 2.63 (2H, q, J¼7.1 Hz, CH2), 1.13 (3H, t,
J¼7.1 Hz, CH3).25
4.3.27. (E)-1-Bromo-4-(4-chlorostyryl)benzene (3dg). dH (250 MHz,
CDCl3) 7.5e7.3 (8H, m, C(6)H), 7.05 (1H, d, J¼16.5 Hz, CH]CH), 6.97
(1H, d, J¼16.5 Hz, CH]CH).44
4.3.28. (E)-Ethyl 3-(2,6-dimethylphenyl)acrylate (3eb). dH (250
MHz, CDCl3) 7.85 (1H, d, J¼16.3 Hz, CH]CH), 7.1e7.0 (3H, m, C(6)
H), 6.07 (1H, d, J¼16.3 Hz, CH]CH), 4.28 (2H, q, J¼7.1 Hz, CH2), 2.36
(6H, s, C(6)CH3), 1.36 (3H, t, J¼7.1 Hz, CH3).45
4.3.14. (E)-1-Methoxy-4-styrylbenzene (3be). dH (250 MHz, CDCl3)
7.5e7.2 (7H, m, C(6)H), 7.08 (1H, d, J¼16.3 Hz, CH]CH), 6.97 (1H, d,
J¼16.3 Hz, CH]CH), 6.9e7.0 (2H, m, C(6)H), 3.84 (3H, s, C(6)OCH3).33
Acknowledgements
4.3.15. (E)-1,2-Bis(4-methoxyphenyl)ethene (3bf). dH (250 MHz,
CDCl3) 7.5e7.4 (4H, m, C(6)H), 6.93 (2H, s, CH]CH), 6.9e6.8 (4H, m,
C(6)H), 3.83 (6H, s, C(6)OCH3).34
This research was supported by the Ministerio de Ciencia e
ꢀ
Innovacion (Projects CTQ2008-05409-C02-01, CTQ2010-20387,
CTQ2011-2264 and Consolider Ingenio 2010 CSD2007-00006),
FEDER, the DURSI-Generalitat de Catalunya (2009SGR-1441), the
Generalitat Valenciana (PROMETEO/2009/038) and the University
4.3.16. (E)-3-(4-Methoxyphenyl)allyl acetate (3bh). dH (250 MHz,
CDCl3) 7.35 (2H, d, J¼8.7 Hz, C(6)H), 6.86 (2H, d, J¼8.7 Hz, C(6)H),
6.62 (1H, d, J¼15.5 Hz, CH]CH), 6.17 (1H, dt, J¼15.5 Hz, 6.7 Hz,
CH]CH), 4.73 (2H, dd, J¼6.7 Hz,1.1 Hz, CH2), 3.83 (3H, s, C(6)OCH3),
2.11 (3H, s, CH3).35
ꢁ
of Alicante. We thank the Universitat Autonoma de Barcelona for
the grant of J.S.
4.3.17. Ethyl cinnamate (3cb). dH (360 MHz, CDCl3) 7.69 (1H, d,
J¼15.8 Hz, CH]CH), 7.5 (2H, m, C(6)H), 7.4e7.3 (3H, m, C(6)H), 6.43
(1H, d, J¼15.8 Hz, CH]CH), 4.26 (2H, q, J¼7.5 Hz, CH2), 1.33 (3H, t,
J¼7.5 Hz, CH3).36
Supplementary data
Supplementary data associated with this article (1H NMR
spectra of compounds 3) can be found in online version. Supple-
mentary data related to this article can be found at http://
4.3.18. tert-Butyl cinnamate (3cc). dH (250 MHz, CDCl3) 7.60 (1H, d,
J 16.1 Hz, CH]CH), 7.5 (2H, m, C(6)H), 7.4e7.3 (3H, m, C(6)H), 6.37
(1H, d, J¼16.1 Hz, CH]CH), 1.54 (9H, s, C(CH3)3).37
References and notes
4.3.19. (E)-1-Phenylpent-1-en-3-one (3cd). dH (250 MHz, CDCl3)
7.6e7.5 (3H, m, C(6)H, CH]CH), 7.4e7.3 (3H, m, C(6)H), 6.74 (1H, d,
1. Wu, A. X.-F.; Anbarasan, P.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2010,
49, 9047e9050.