R. Bera et al. / Tetrahedron 65 (2009) 1300–1305
1305
4.14. 3-(3-Ethoxy-phenyl)-acrylic acid ethyl ester (7c)
References and notes
Light yellow oil; Rf (10% ethyl acetate in n-hexane): 0.52; 1H
1. Brunet, M.; Zeiller, J.-J.; Berthelon, J.-J.; Contard, F.; Augert, G.; Guerrier, D. US
Patent Application US 6596758 B1, Jul 22, 2003.
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NMR (DMSO-d6, 400 MHz)
d
7.66–7.62 (m, 2H), 7.6 (d, J¼15.6 Hz,
1H), 6.95 (d, J¼8.8 Hz, 2H), 6.47 (d, J¼16.0 Hz, 1H), 4.18 (q, J¼7.6 Hz,
2H), 1.3 (t, J¼7.6 Hz, 3H), 1.25 (t, J¼7.2 Hz, 3H); IR (cmꢁ1, KBr) 2980,
2934, 1708, 1604, 1251, 1172, 1403, 826; m/z (ES Mass) 221 (Mþ1,
100%); 13C NMR (DMSO-d6, 200 MHz)
d 166.3, 160.3, 144.0, 129.9
(2C), 126.4, 115.2, 114.7 (2C), 63.22 (CH2), 59.7 (CH2), 14.5 (CH3), 14.2
(CH3); HPLC 99.69%, Column: Xterra MS C18 (150ꢂ4.6 mm), mobile
phase A: 0.05% TFA in water, mobile phase B: 0.05% TFA in aceto-
nitrile, gradient (T/%B)¼0/0, 30/85, 35/85, 36/0, flow 1.0 mL/min;
UV 215 nm, retention time 16.0 min; HRMS (ESI): calcd for
C13H16O3 (MþH)þ 221.1178, found 221.1188.
6. For review, see: Caddick, S. Tetrahedron 1995, 51, 10403.
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4.15. 3-(3-Bromo-phenyl)-acrylic acid ethyl ester (7d)
This compound was obtained as off white solid; mp 36–38 ꢀC;
Rf (20% ethyl acetate in n-hexane): 0.75; 1H NMR (DMSO-d6,
400 MHz)
d
7.97 (s, 1H), 7.4 (d, J¼7.6 Hz, 1H), 7.64–7.6 (m, 2H), 7.37
(t, J¼8.0 Hz,1H), 6.73 (d, J¼16.0 Hz,1H), 4.2 (q, J¼7.2 Hz, 2H),1.26 (t,
J¼6.8 Hz, 3H); IR (cmꢁ1, KBr) 2979, 1709, 1641, 1556, 1310, 1180,
1035, 785; m/z (ES Mass) 255 (M), 257 (Mþ2); 13C NMR (DMSO-d6,
200 MHz)
d 171.2, 148, 141.8, 138.2, 136.2, 136.1, 132.5, 127.6, 125.2,
65.5 (CH2), 19.5 (CH3); HPLC 99.7%, Column: ZORBAX XDB-C8
(150ꢂ4.6 mm), mobile phase A: 0.05% TFA in water, mobile phase B:
0.05% TFA in acetonitrile, gradient (T/%B)¼0/15, 25/90, 30/90, 31/
35, flow 1 mL/min; UV 215 nm, retention time 19.4 min; HRMS
(ESI): calcd for C11H12BrO2 255.0021, found 255.0031.
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4.16. 3-Chloro phenyl-acrylic acid ethyl ester (7e)
This compound was obtained as off white colored low melting
31. Craig, D.; Martin, M. L. Molecules 1998, 3, 64.
solid; mp 33–35 ꢀC; Rf (20% ethyl acetate in n-hexane): 0.7; 1H NMR
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(DMSO-d6, 400 MHz)
d
7.84 (s, 1H), 7.7 (d, J¼7.6 Hz, 1H), 7.65 (d,
J¼16.4 Hz, 1H), 7.49–7.42 (m, 2H), 6.72 (d, J¼16.0 Hz, 1H), 4.2 (q,
J¼7.2 Hz, 2H), 1.26 (t, J¼7.6 Hz, 3H); IR (cmꢁ1, KBr) 2982, 2903, 1713,
1640, 1566, 1313, 1201, 1180, 1036, 787; m/z (ES Mass) 211; 13C NMR
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505.
(DMSO-d6, 200 MHz)
d 165.8, 142.5, 136.1, 133.6, 130.4, 129.8, 127.7,
126.7, 119.7, 60.0 (CH2), 40.0 (CH3); HPLC 99.4%, Column: Xterra MS
C18 (150ꢂ4.6 mm), mobile phase A: 0.05% TFA in water, mobile
phase B: 0.05% TFA in acetonitrile, gradient (T/%B)¼0/0, 30/85, 35/
85, 36/0, flow 1 mL/min, UV 215 nm, retention time 16.8 min;
HRMS (ESI): calcd for C11H12ClO2 211.0526, found 211.0527.
40. Tamura, R.; Saegusa, K.; Kakihana, M.; Oda, D. J. Org. Chem. 1988, 53, 2723.
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Aggarwal, V. K.; Harvey, J. N. J. Am. Chem. Soc. 2005, 127, 13468; (b) Vedejs, E.;
Peterson, M. J. Top. Stereochem. 1994, 21, 1; (c) Vedejs, E.; Peterson, M. J. In
Advances in Carbanion Chemistry; Snieckus, V., Ed.; JAI: Greenwich, CN, 1996;
Vol. 2.
Acknowledgements
The authors thank Dr. V. Dahanukar and Mr. A. Mukherjee of DRL
for their encouragement and the analytical group for spectral data.