Molecules 2013, 18
10275
(E)-3-(3,4-Dichlorophenyl)-2-butenoic acid ethyl ester [(E)-5e]. Yield 78%; IR (neat):
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ν (cm−1) = 1711, 1630, 1469, 1277, 1169; H-NMR (CDCl3): δ (ppm) = 1.21 (t, J = 7.03 Hz, 3H,
CH3–CH2–), 2.42 (d, J = 1.23 Hz, 3H, 4-H), 4.12 (q, J = 7.03 Hz, 2H, –CH2–CH3), 5.99 (q, J = 1.23 Hz,
1H, 2-H), 7.10–7.44 (m, 3H, Harom.); 13C-NMR (CDCl3): δ (ppm) = 14.7 (CH3–CH2–), 18.1 (C-4), 60.5
(–CH2–CH3), 118.8 (C-2), 125.9, 128.7, 130.8, 133.2, 133.4, 142.5 (Carom.), 152.9 (C-3), 166.7 (C-1).
(Z)-3-(3,4-Dichlorophenyl)-2-butenoic acid ethyl ester [(Z)-5e]. Yield 6%; IR (neat): ν (cm−1) = 1717,
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1644, 1472, 1229, 1165; H-NMR (CDCl3): δ (ppm) = 1.16 (t, J = 7.00 Hz, 3H, CH3–CH2–), 2.17 (d,
J = 1.53 Hz, 3H, 4-H), 4.07 (q, J = 7.00 Hz, 2H, –CH2–CH3), 5.96 (q, J = 1.53 Hz, 1H, 2-H),
7.05–7.46 (m, 3H, Harom.). 13C-NMR (CDCl3): δ (ppm) = 14.4 (CH3–CH2–), 27.3 (C-4), 60.5 (CH2–CH3),
119.4 (C-2), 126.9, 129.3, 130.3, 132.1, 132.5, 141.1 (Carom.), 152.9 (C-3) 165.8 (C-1).
(E)-3-(4-Fluorophenyl)-2-butenoic acid ethyl ester [(E)-5f] [27]. Yield 69%; IR (neat): ν (cm−1) = 1710,
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1631, 1602, 1508, 1233, 1157; H-NMR (CDCl3): δ (ppm) = 1.32 (t, J = 7.03 Hz, 3H, CH3–CH2–),
2.57 (d, J = 1.23 Hz, 3H, 4-H), 4.22 (q, J = 7.03 Hz, 2H, –CH2–CH3), 6.10 (q, J = 1.23 Hz, 1H, 2-H),
7.02–7.11 (m, 2H, Harom.), 7.43–7.49 (m, 2H, Harom.). 13C-NMR (CDCl3): δ (ppm) = 14.7 (CH3–CH2–),
18.3 (C-4), 60.3 (CH2–CH3), 115.8 (d, JC-3`, F& C-5`, F = 21.99 Hz, C-3` and C-5`), 117.5 (C-2),
128.5 (d, JC-2`, F& C-6`,F = 7.64 Hz, C-2` and C-6`), 138.6 (d, JC-1`, F = 2.87 Hz, C-1`), 154.6 (C-3), 163.6
(d, JC-4`, F = 249.45 Hz, C-4`), 167.1 (C-1).
(Z)-3-(4-Fluorophenyl)-2-butenoic acid ethyl ester [(Z)-5f]. Yield 10%; IR (neat): ν (cm−1) = 1718,
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1638, 1603, 1509, 1226, 1153; H-NMR (CDCl3): δ (ppm) = 1.00 (t, J = 7.00 Hz, 3H, CH3–CH2–),
2.05 (d, J= 1.53 Hz, 3H, 4-H), 3.89 (q, J = 7.00 Hz, 2H, –CH2–CH3), 5.79 (q, J = 1.53 Hz, 1H, 2-H),
6.86–6.97 (m, 2H, Harom. ), 7.04–7.12 (m, 2H, Harom.). 13C-NMR (CDCl3): δ (ppm) = 14.4 (CH3–CH2–),
27.6 (C-4), 60.2 (–CH2–CH3), 115.3 (d, JC-3`, F& C-5`, F = 21.98 Hz, C-3`and C-5`), 118.5 (C-2),
129.2 (d, JC-2`, F& C-6`, F = 7.60 Hz, C-2` and C-6`), 137.0 (d, JC-1`, F = 3.82 Hz, C-1`), 154.7 (C-3),
162.8 (d, JC-4`, F = 247.41 Hz, C-4`), 166.2 (C-1).
(E)-3-(3-Methoxyphenyl)-2-butenoic acid ethyl ester [(E)-5g] [28]. Yield 82%; IR (neat): ν (cm−1) = 1709,
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1627, 1578, 1216, 1156; H-NMR (CDCl3): δ (ppm) = 1.35 (t, J = 7.03 Hz, 3H, CH3–CH2–), 2.59 (d,
J = 1.23 Hz, 3H, 4-H), 3.85 (s, 3H, OCH3), 4.25 (q, J = 7.03 Hz, 2H, –CH2–CH3), 6.16 (q, J = 1.23 Hz,
1H, 2-H), 6.19–7.34 (m, 4H, Harom.). 13C-NMR (CDCl3): δ (ppm) = 14.7 (CH3–CH2–), 18.4 (C-4), 55.7
(OCH3), 60.3 (–CH2–CH3), 112.5 (C-2), 114.7, 117.7, 119.2, 129.9, 144.2 (Carom.), 155.8 (C-3), 160.0
(Carom. ), 167.2 (C-1).
(Z)-3-(3-Methoxyphenyl)-2-butenoic acid ethyl ester [(Z)-5g]. Yield 9%; IR (neat): ν (cm−1) = 1724,
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1599, 1578, 1213, 1151; H-NMR (CDCl3): δ (ppm) = 1.13 (t, J = 7.00 Hz, 3H, CH3–CH2–), 2.20 (d,
J = 1.53 Hz, 3H, 4-H), 3.83 (s, 3H, OCH3), 4.04 (q, J = 7.00 Hz, 2H, –CH2–CH3), 5.93 (q, J = 1.53 Hz,
1H, 2-H), 6.77–7.33 (m, 4H, Harom.). 13C-NMR (CDCl3): δ (ppm) = 14.4 (CH3–CH2–), 27.5 (C-4), 55.6
(OCH3), 60.2 (–CH2–CH3), 113.1 (C-2), 113.4, 118.3, 119.7, 129.4, 142.7 (Carom.), 155.3 (C-3), 159.6
(Carom.), 166.3 (C-1).