J. CHEM. RESEARCH (S), 1998 643
J 7.1), 4.22 (q, 2H, J 7.1), 6.95±7.05 (m, 2H), 7.20±7.37 (m, 2H),
Methyl (E)-4-(4-¯uorophenyl)-3-methoxycarbonylbut-3-enoate 4j.
ÐYield, 68%, Oil; ꢂmax/cm 1; 2950, 1710, 1640, 1440, 1370, 1270,
1020; ꢃH 3.52 (s, 2H), 3.74 (s, 3H), 3.83 (s, 3H), 7.06±7.12 (m, 2H),
7.26±7.37 (m, 2H), 7.86 (s, 1H); m/z 252 (M , 75%), 221 (87), 220
(66), 192 (25), 149 (21), 133 (100). (Found: C, 61.97; H, 5.43.
7.73 (s, 1H); m/z 281 (M 1, 13%), 280 (M , 49), 235 (89), 234
(51), 206 (35), 134 (64), 133 (100), 115 (15). (Found: C, 63.94;
H, 6.25. C15H17FO4 requires C, 64.28; H, 6.11%).
Ethyl (E)-4-(4-methylphenyl)-3-ethoxycarbonylbut-3-enoate 4c.Ð
Yield, 71%. Bp 161 8C at 1 mmHg (lit.,5 bp 135±138 8C at 0.4
Torr); ꢂmax/cm 1; 2980, 1740, 1640, 1450, 1270, 1130, 1030; ꢃH 1.26
(t, 3H, J 7.1), 1.33 (t, 3H, J 7.1), 2.36 (s, 3H), 3.53 (s, 2H), 4.20 (q,
2H, J 7.1), 4.22 (q, 2H, J 7.1), 7.11±7.35 (m, 4H), 7.87 (s, 1H); m/z
C
13H13FO4 requires C, 61.90; H, 5.19%).
Methyl (E)-4-(4-methylphenyl)-3-methoxycarbonylbut-3-enoate 4k.
ÐYield, 66%. Bp 142 8C at 1 mmHg (lit.,5 bp 138 8C at Torr);
ꢂ
max/cm 1; 2950, 1740, 1640, 1440, 1280, 1020; ꢃH 2.37 (s, 3H), 3.56
(s, 2H), 3.73 (s, 3H), 3.82 (s, 3H), 7.19±7.26 (m, 4H), 7.88 (s, 1H);
276 (M , 72%), 231 (44), 230 (68), 202 (52), 131 (98), 129 (100),
115 (38), 99 (26).
m/z 249 (M 1, 35%), 248 (M , 100), 217 (98), 188 (11), 129 (36),
115 (9).
Ethyl (E)-4-(4-bromophenyl)-3-ethoxycarbonyl-3-enoate 4d.ÐYield,
70%. Oil; ꢂmax/cm 1; 2980, 1740, 1640, 1450, 1280, 1180, 1030; ꢃH
1.26 (t, 3H, J 7.1), 1.32 (t, 3H, J 7.1), 3.47 (s, 2H), 4.17 (q, 2H,
J 7.1), 4.28 (q, 2H, J 7.1), 7.21 (dd, 2H, J 1.7, 5.0 Hz), 7.50 (dd,
Methyl (E)-4-(4-bromophenyl)-3-methoxycarbonylbut-3-enoate 4l.
ÐYield, 70%; Oil; ꢂmax/cm 1; 2950, 1720, 1640, 1490, 1280, 1210,
1050; ꢃH 3.49 (s, 2H), 3.73 (s, 3H), 3.82 (s, 3H), 7.23 (d, 2H, J 8.4),
7.51 (d, 2H, J 8.4), 7.81 (s, 1H); m/z 314 (M 1, 100%), 313
2H, J 1.8, 5.0 Hz), 7.80 (s, 1H); m/z 342 (M 1, 68%), 341 (M ,
(M , 28), 312 (95), 283 (63), 281 (63), 201 (41), 174 (54), 115
(88) (Found: C, 49.86; H, 4.17. C13H13BrO4 requires C, 49.86;
H, 4.18%).
26), 340 (M
1, 65), 297 (100), 295 (96), 188 (50), 160 (13), 129
(27), 115 (93) (Found: C, 52.80; H, 5.11. C15H17BrO4 requires
C, 52.80; H, 5.02%).
Methyl
(E)-4-(4-tri¯uoromethylphenyl)-3-methoxycarbonylbut-3-
Ethyl (E)-4-(4-tri¯uoromethylphenyl)-3-ethoxycarbonylbut-3-enoate
4e.ÐYield, 65%. Oil; ꢂmax/cm 1; 2950, 1720, 1620, 1500, 1330,
1170, 1020; ꢃH 1.27 (t, 3H, J 7.1), 1.34 (t, 3H, J 7.1), 3.47 (s, 2H),
4.18 (q, 2H, J 7.1), 4.30 (q, 2H, J 7.1), 7.45 (d, 2H, J 8.2), 7.64
enoate 4m.ÐYield, 63%. Oil; ꢂmax/cm 1; 2950, 1720, 1620, 1440,
1330, 1170, 1050; ꢃH 3.49 (s, 2H), 3.74 (s, 3H), 3.84 (s, 3H), 7.47
(d, 2H, J 8.2), 7.64 (d, 2H, J 8.2), 7.91 (s, 1H); m/z 303 (M 1,
12%), 302 (M , 44), 283 (24), 270 (100), 242 (45), 183 (58), 164
(19), 115 (44) (Found: C, 55.49; H, 4.33. C14H13F3O4 requires
C, 55.63; H, 4.34%).
(d, 2H, J 8.2), 7.89 (s, 1H); m/z 331 (M 1, 33%), 286 (20), 285
(100), 165 (8), 115 (8) (Found: C, 58.03; H, 5.24. C16H17F3O4
requires C, 58.18; H, 5.19%).
Ethyl (E)-4-phenyl-3-ethoxycarbonylbut-3-enoate 4f.ÐYield, 65%.
We thank the National Science Foundation of China and
Academia Sinica for ®nancial support.
1
Bp 158 8C at 1 mmHg (lit.,5 bp 132±134 8C at 0.4 Torr); ꢂmax/cm
;
2980, 1740, 1640, 1450, 1270, 1130; ꢃH 1.27 (t, 3H, J 7.1), 1.33
(t, 3H, J 7.1), 3.52 (s, 2H), 4.17 (q, 2H, J 7.1), 4.27 (q, 2H, J 7.1),
7.30±7.42 (m, 5H), 7.89 (s, 1H), m/z 263 (M 1, 33%), 262 (M ,
Received, 11th March 1998; Accepted, 9th June 1998
Paper E/8/03769H
100), 231 (83), 216 (28), 130 (39), 129 (70).
Ethyl (E)-3-ethoxycarbonylhept-3-enoate 4g.ÐYield, 65%. Oil;
ꢂ
max/cm 1; 2980, 1730, 1650, 1450, 1330, 1240, 1040; ꢃH 0.92 (t, 3H,
J 7.4), 1.22 (t, 3H, J 7.1), 1.24 (t, 3H, J 7.1), 1.40±1.53 (m, 2H),
2.15 (m, 2H), 3.31 (s, 2H), 4.11 (q, 2H, J 7.1), 4.17 (q, 2H, J 7.1),
References
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6.94 (d, 1H, J 7.6); m/z 229 (M 1, 40%), 184 (17), 183 (100), 182
(27), 155 (15), 154 (13) (Found: C, 63.05; H, 9.04. C12H20O4
requires C, 63.14; H, 8.83%).
Ethyl (E)-4-(2-furyl)-3-ethoxycarbonylbut-3-enoate 4h.ÐYield,
64%. Bp 137 8C at 1 mmHg (lit.,5 bp 120±121 8C at 0.5 Torr);
ꢂ
max/cm 1; 3130, 2980, 1730, 1700, 1480, 1210, 1100; ꢃH 1.21 (t, 3H,
J 7.2), 1.31 (t, 3H, J 7.2), 3.84 (s, 2H), 4.14 (q, 2H, J 7.1), 4.27
(q, 2H, J 7.1), 6.47 (dd, 1H, J 1.7, 3.4), 6.64 (d, 1H, J 3.4), 7.51
(d, 1H, J 1.7), 7.53 (s, H); m/z 252 (M , 87%), 207 (61), 179 (100),
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38, 5775.
151 (46), 106 (34), 79 (44).
Methyl (E)-4-(4-chlorophenyl)-3-methoxycarbonylbut-3-enoate 4i.
ÐYield, 68%. Bp 165 8C at 1 mmHg (lit.,5 bp, 133±134 8C at
0.3 Torr); ꢂmax/cm 1; 2960, 1740, 1640, 1440, 1260, 1040; ꢃH 3.49
(s, 2H), 3.72 (s, 3H), 3.82 (s, 3H), 7.29 (d, 2H, J 8.5), 7.34 (d, 2H,
7 L. F. Tietze and U. Beifuss, Angew. Chem., Int. Ed. Engl., 1993,
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J 8.5), 7.83 (s, 1H); m/z 269 (M 1, 37%), 268 (M , 100), 239 (36),
237 (95), 236 (44), 150 (8), 149 (23), 115 (23).