10.1002/adsc.201801660
Advanced Synthesis & Catalysis
Anal. Calcd. for C19H16O2S (308.39): C, 74.00; H, 5.23; S,
10.40. Found: C, 74.04; H, 5.20; S, 10.37.
The authors thank the University of Camerino for the financial
support.
Methyl 5-phenethylthiophene-2-carboxylate 4f. White
solid, mp: 50-52°C. IR (cm-1, neat): 740, 824, 1091, 1254,
References
1
1461, 1703, 3009, 3033. H-NMR (CDCl3, 400MHz) δ:
2.97-3.03 (m, 2H), 3.12-3.18 (m, 2H), 3.86 (s, 3H), 6.75 (d,
1H, J = 3.8 Hz), 7.15-7.33 (m, 5H), 7.62 (d, 1H, J = 3.8
Hz). 13C-NMR (CDCl3, 100MHz) δ: 32.5, 37.8, 52.2, 125.8,
126.6, 128.6, 128.7, 131.1, 133.9, 140.6, 152.7, 163.0. GC-
MS (70 eV): m/z: 246 ([M+], 31), 155 (100), 126 (10), 91
(47), 65 (48). Anal. Calcd. for C14H14O2S (246.32): C,
68.27; H, 5.73; S, 13.02. Found: C, 68.32; H, 5.77; S,
12.98.
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Benzyl 5-methylthiophene-2-carboxylate 4g. Pale yellow
oil. IR (cm-1, neat): 744, 814, 1035, 1076, 1268, 1371,
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1451, 1691. H-NMR (CDCl3, 400MHz) δ: 2.52 (s, 3H),
RSC Adv. 2015, 5, 4210-4213.
5.32 (s, 2H), 6.76 (d, 1H, J = 3.8 Hz), 7.30-7.46 (m, 5H),
7.65 (d, 1H, J = 3.8 Hz). 13C-NMR (CDCl3, 100MHz) δ:
16.0, 66.7, 126.6, 128.3, 128.4, 128.8, 131.1, 134.4, 136.2,
148.5, 162.3. GC-MS (70 eV): m/z: 232 ([M+], 45), 187
(11), 125 (100), 91 (48). Anal. Calcd. for C13H12O2S
(232.30): C, 67.22; H, 5.21; S, 13.80. Found: C, 67.17; H,
5.18; S, 13.76.
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Butyl thiophene-2-carboxylate 4h. Pale yellow oil. IR
1
(cm-1, neat): 750, 1092, 1257, 1419, 1526, 1705. H-NMR
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(CDCl3, 400MHz) δ: 0.97 (t, 3H, J = 7.3 Hz), 1.40-1.41 (m,
2H), 1.65-1.77 (m, 2H), 4.30 (t, 2H, J = 6.8 Hz), 7.08-7.11
(m, 1H), 7.53-7.55 (m, 1H), 7.78-7.80 (m, 1H). 13C-NMR
(CDCl3, 100MHz) δ: 14.0, 19.4, 31.0, 65.2, 127.9, 132.4,
133.5, 134.3, 162.6. GC-MS (70 eV): m/z: 184 ([M+], 9),
128 (60), 111 (100), 83 (8), 56 (8), 39 (19). Anal. Calcd.
for C9H12O2S (184.25): C, 58.67; H, 6.56; S, 17.40. Found:
C, 58.62; H, 6.60; S, 17.37.
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Butyl 5-ethylthiophene-2-carboxylate 4i. Pale yellow oil.
IR (cm-1, neat): 750, 1089, 1253, 1278, 1449, 1526, 1705.
1H-NMR (CDCl3, 400MHz) δ: 0.96 (t, 3H, J = 7.3 Hz),
1.32 (t, 3H, J = 7.3 Hz), 1.39-1.50 (m, 2H), 1.67-1.75 (m,
2H), 2.86 (q, 2H, J = 7.3 Hz), 4.26 (t, 2H, J = 6.8 Hz),
6.77-6.79 (m, 1H), 7.63 (d, 1H , J = 3.8 Hz). 13C-NMR
(CDCl3, 100MHz) δ: 14.0, 15.9, 19.4, 24.1, 31.0, 65.0,
124.7, 131.2, 133.7, 155.6, 162.7. GC-MS (70 eV): m/z:
212 ([M+], 20), 156 (78), 141 (100), 139 (90), 124 (7), 111
(14). Anal. Calcd. for C11H16O2S (212.31): C, 62.23; H,
7.60; S, 15.10. Found: C, 62.27; H, 7.57; S, 15.13.
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Propyl 5-heptylthiophene-2-carboxylate 4j. Pale yellow
oil. IR (cm-1, neat): 733, 748, 1086, 1258, 1281, 1461,
1
1708. H-NMR (CDCl3, 400MHz) δ: 0.88 (t, 3H, J = 7.3
Hz), 1.00 (t, 3H, J = 7.3 Hz), 1.21-1.41 (m, 8H), 1.62-1.81
(m, 4H), 2.82 (t, 2H, J = 7.7 Hz), 4.22 (t, 2H, J = 6.8 Hz),
6.77 (d, 1H, J = 3.8 Hz), 7.62 (d, 1H, J = 3.8 Hz). 13C-
NMR (CDCl3, 100MHz) δ: 10.7, 14.3, 22.4, 22.9, 29.2,
30.7, 31.7, 32.0, 66.7, 125.3, 131.2, 133.7, 154.2, 162.7.
GC-MS (70 eV): m/z: 268 ([M+], 45), 209 (64), 183 (96),
141 (100), 97 (51), 43 (25). Anal. Calcd. for C15H24O2S
(268.41): C, 67.12; H, 9.01; S, 11.94. Found: C, 67.17; H,
9.05; S, 11.91.
Propyl 5-(p-tolyl)thiophene-2-carboxylate 4k. White
solid, mp: 54-56°C. IR (cm-1, neat): 747, 806, 1086, 1234,
1263, 1344, 1447, 1539, 1701. 1H-NMR (CDCl3, 400MHz)
δ: 1.03 (t, 3H, J = 7.3 Hz), 1.72-1.85 (m, 2H), 2.38 (s, 3H),
4.26 (t, 2H, J = 6.8 Hz) 7.21 (d, 2H, 8.1 Hz), 7.25 (d, 1H, J
= 3.8 Hz), 7.53 (d, 2H, J = 8.1 Hz), 7.74 (d, 1H, J = 3.8
Hz). 13C-NMR (CDCl3, 100MHz) δ: 10.7, 21.5, 22.4, 66.9,
123.3, 126.3, 130.0, 131.0, 132.2, 134.4, 139.1, 151.6,
162.6. GC-MS (70 eV): m/z: 260 ([M+], 71), 218 (100),
201 (67), 173 (18), 129 (40). Anal. Calcd. for C15H16O2S
(260.35): C, 69.20; H, 6.19; S, 12.31. Found: C, 69.25; H,
6.22; S, 12.34.
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Acknowledgements
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