9
00
E. Metay, E. L e´ onel, and J.-Y. N e´ d e´ lec
1
6
48.5, 146.7, 144.8, 136.8, 134.6, 127.8, 125.9, 120.6, 109.9, 105.3, 101.3,
0.3, 44.9, 30.0, 26.9, 14.3; MS (EI) M/Z (%): 317 (12), 316 (57), 258
(
31), 245 (21), 229 (21), 225 (13), 213 (21), 212 (24), 201 (11), 199 (19),
86 (15), 185 (100), 183 (11), 173 (26), 169 (13), 141 (12), 115 (18); IR
1
vmax: 3054, 2984, 2900, 1708, 1614, 1504, 1484; HRMS (ESI) m/z calcd.
for C H O Na (M þ Na): 339.1208; found: 339.1225.
1
8 20 5
Ethyl (E,E)-5-[6-Methyl-2-(3-oxobutyl)-3-quinolyl]penta-2.4-dienoate 14
1
Yield 63%; H NMR (CDCl , 300 MHz) d: 8.07 (s, 1H), 7.83 (d, J ¼ 8.5 Hz,
3
1
1
3
H), 7.55–7.45 (m, 3H), 7.23 (d, J ¼ 15.3 Hz, 1H), 6.87 (dd, J ¼ 15.3,
1.1 Hz, 1H), 6.05 (d, J ¼ 15.3 Hz, 1H), 4.27 (q, J ¼ 7.1 Hz, 2H), 3.52–
.45 (m, 2H), 3.31–3.27 (m, 2H), 2.50 (s, 3H), 2.33 (s, 3H), 1.35
1
3
(
t, J ¼ 7.1 Hz, 3H); C NMR (CDCl , 75 MHz) d: 208.3, 166.8, 157.1,
3
1
1
45.9, 143.5, 136.1, 135.8, 132.0, 131.8, 129.5, 128.3, 126.5, 128.9, 126.9,
22.4, 60.5, 40.5, 30.4, 29.6, 21.5, 14.3; MS (EI) M/Z (%): 337 (26), 323
(
10), 322 (47), 308 (38), 295 (29), 294 (100), 280 (20), 266 (33), 264 (18),
48 (32), 222 (16), 221 (14), 220 (54), 207 (22), 206 (15), 194 (61), 181
14); IR vmax: 3041, 2979, 1723, 1628; HRMS (ESI) m/z calcd. for
C H NO (M þ H): 338.1756; found: 338.1757.
2
(
2
1
24
3
Ethyl 3-[5-Fluoro-2-(3-hydroxybutyl)phenyl]propanoate 15
1
Yield 82%; H NMR (CDCl , 300 MHz) d: 7.14 (dd, J ¼ 8.2, 6.3 Hz, 1H),
3
6
2
1
1
.89–6.82 (m, 2H, H ), 4.16 (q, J ¼ 7.1 Hz, 2H), 3.92–3.81 (m, 1H), 3.00–
7
.95 (m, 2H), 2.83–2.58 (m, 4H), 2.44 (se, 1H), 1.76–1.68 (m, 2H), 1.29–
¼ 243.5 Hz)
1
.24 (m, 6H); C NMR (CDCl , 75 MHz) d: 172.9, (d, J
3
1
3
CF
3
61.2, (d, J
4
3
¼ 7.0 Hz, C ) 140.3, (d. J
¼ 3.0 Hz) 135.7, (d, J
CF
6
CF
CF
2
7.9 Hz) 130.6, (2d, J
¼
¼ 21.0 Hz, 20.7 Hz) 115.3 and 113.2, 67.4,
¼ 1.3 Hz) 27.5, 23.7, 14.2; MS (EI) M/Z
CF
4
0.7, 40.6, 35.0, 28.1, (d, J
%): 268 (14), 250 (38), 205 (11), 204 (44), 189 (12), 181 (11), 178 (12),
6
CF
(
1
77 (21), 176 (70), 175 (17), 165 (11), 164 (14), 163 (22), 162 (55), 161
89), 160 (16), 159 (12), 151 (32), 150 (12), 149 (76), 148 (22), 147 (100),
46 (45), 137 (17), 136 (25), 135 (83), 134 (24), 133 (33), 123 (18), 122
12), 115 (41), 109 (22); IR vmax: 3462, 3032, 1727; HRMS (ESI) m/z
calcd. for C H FO (M þ H): 269.1553; found: 269.1561.
(
1
(
1
5
22
3
Ethyl 3-[2-(3-Hydroxybutyl)-6-methoxy-3-quinolyl]propanoate 16
1
Yield 71%; H NMR (CDCl 300 MHz) d: 7.93 (d, J ¼ 9.2 Hz, 1H), 7.84
3
(
s, 1H), 7.31 (dd, J ¼ 9.2, 2.8 Hz, 1H), 7.02 (d, J ¼ 2.8 Hz, 1H), 4.18
q, J ¼ 7.1 Hz, 2H), 3.95–3.87 (m, 4H), 3.30–3.08 (m, 4H), 2.76–2.70
m, 2H), 2.10–1.97 (m, 2H), 1.29 (d, J ¼ 6.3 Hz, 3H), 1.27 (t, J ¼ 7.1 Hz,
(
(
1
3
3
H); C NMR (CDCl , 75 MHz) d: 172.5, 158.3, 157.8, 141.8, 134.5,
3
132.3, 129.4, 128.0, 121.7, 104.7, 67.6, 60.7, 55.5, 36.7, 34.4, 31.7, 27.5,