Arkivoc 2019, v, 0-0
Teimuri-Mofrad, R. et al.
86 Methoxyethyl) 6-ethyl 4-oxo-4H-pyran-2,6-dicarboxylate (7e). Yellow oil (0.12 g, 19%, Rf = 0.51). IR (KBr, νmax
,
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87 cm-1): 2995, 2893, 1752, 1665, 1410, 1378, 1348, 1265, 1138, 765. H NMR (400 MHz, CDCl3): δH 1.28 (3H, t,
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88 3JHH 6.5 Hz, -OCH2CH3), 3.41 (3H, s, -OCH2CH3), 3.71-3.74 (2H, m, -CH2OCH3), 4.21 (2H, q, JHH 6.5 Hz,
89 CH3CH2OCO-), 4.48-4.52 (2H, m, -COOCH2-), 7.15 (2H, s, pyran-CH-3, -5). 13C NMR (100 MHz, CDCl3): δC 13.8 (-
90 COOCH2CH3), 59.4 (CH3OCH2-), 61.0 (-COOCH2CH3), 68.1 (-COOCH2CH2-), 71.1 (-COOCH2CH2), 120.0 (pyran-C-5),
91 120.3 (pyran-C-3), 152.5 (pyran-C-6), 153.6 (pyran-C-2), 159.2 (-COOC2H5), 160.1 (-COOCH2CH2-), 180.1 (pyran-
92 C-4). MS: m/z 270 (M+). Anal. calcd. for C12H14O7: C, 53.34%; H, 5.22%. Found: C, 53.23%; H, 5.13%.
93 Reaction of compound 4a with ethylene glycol monomethyl ether (5b)
94 Diethyl chelidonate (4a) (0.53 g, 2.5 mmol) and ethylene glycol monomethyl ether (5b) (0.68 g, 7.5 mmol)
95 were reacted according to the general procedure. Compounds 6b and 7b were obtained.
96 Bis(2-ethoxyethyl) 4-oxo-4H-pyran-2,6-dicarboxylate (6b). Yellow oil (0.50 g, 61%, Rf = 0.75). IR (KBr, νmax, cm-
97 1): 2937, 2887, 1757, 1665, 1412, 1373, 1342, 1267, 1215, 1130, 1035, 962, 765. 1H NMR (400 MHz, CDCl3): δH
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98 1.22 (3H, s, JHH 7 Hz, -OCH2CH3), 3.43 (2H, q, JHH 7 Hz, CH3CH2O-Å), 3.71-3.75 (4H, m, -CH2OC2H5), 4.48-4.53
99 (4H, m, -COOCH2-), 7.2 (2H, s, pyran-CH-3, -5). 13C NMR (100 MHz, CDCl3): δC 15.1 (-OCH2CH3), 66.1 (-OCH2CH3),
00 67.1 (-COOCH2CH2-), 71.1 (-COOCH2CH2-), 121.5 (pyran-C-3, -5), 154.0 (pyran-C-2, -6), 160.3 (-COOCH2CH2),
01 180.2 (pyran-C-4). MS: m/z 328 (M+). Anal. calcd. for C15H20O8: C, 54.88%; H, 6.14%. Found: C, 54.75%; H,
02 5.98%.
03 2-(2-Ethoxyethyl) 6-methyl 4-oxo-4H-pyran-2,6-dicarboxylate (7b). Yellow oil (0.09 g, 14%, Rf = 0.57). IR (KBr,
04 νmax, cm-1): 2989, 2887, 1754, 1663, 1408, 1372, 1347, 1273, 1120, 762. 1H NMR (400 MHz, CDCl3): δH 1.22 (3H,
05 t, J = 7 Hz, OCH2CH3), 3.41 (2H, q, J = 7 Hz, -OCH2CH3), 3.70-3.74 (2H, m, -CH2OC2H5), 4.01 (3H, s, -COOCH3),
06 4.50-4.53 (2H, m, -COOCH2-), 7.19 (2H, s, pyran-CH-3, -5). 13C NMR (100 MHz, CDCl3): δC 15.0 (-CH2OCH2CH3),
07 66.2 (-CH2OCH2CH3), 68.1 (-COOCH2CH2-), 70.3 (-COOCH3), 71.2 (-COOCH2CH2-), 120.1 (pyran-C-5), 120.3
08 (pyran-C-3), 152.5 (pyran-C-6), 153.6 (pyran-C-2), 159.2 (-COOCH3), 160.1 (-COOCH2CH2-), 179.9 (pyran-C-4).
09 MS: m/z 270 (M+). Anal. calcd. for C12H14O7: C, 53.34%; H, 5.22%. Found: C, 53.25%; H, 5.16%.
10 Reaction of compound 4b with ethylene glycol monomethyl ether (5b)
11 Diethyl chelidonate (4b) (0.60 g, 2.5 mmol) and ethylene glycol monomethyl ether (5b) (0.68 g, 7.5 mmol)
12 were reacted according to the general procedure. Compounds 6b and 7f were obtained.
13 Bis(2-ethoxyethyl) 4-oxo-4H-pyran-2,6-dicarboxylate (6b). Yellow oil (0.55 g, 67%) was obtained; The spectral
14 properties were identical to that of compound 6b reported earlier (see Section 2.3.1.).
15 2-(2-Ethoxyethyl) 6-ethyl 4-oxo-4H-pyran-2,6-dicarboxylate (7f). Yellow oil (0.08 g, 11%, Rf = 0.49). IR (KBr,
16 νmax, cm-1): 2991, 2887, 1739, 1661, 1401, 1371, 1340, 1251, 1145, 751. 1H NMR (400 MHz, CDCl3): δH 1.21 (3H,
17 t, 3JHH 7 Hz, -OCH2CH3), 1.29 (3H, t, 3JHH 6.5 Hz, -COOCH2CH3), 3.43 (2H, q, 3JHH 7 Hz, -OCH2CH3), 3.69-3.72 (2H,
3
18 m, -CH2OC2H5), 4.22 (2H, q, JHH 6.5 Hz, -COOCH2CH3), 4.49-4.53 (2H, m, -COOCH2-), 7.17 (2H, s, pyran-CH-3, -
19 5). 13C NMR (100 MHz, CDCl3): δC 13.9 (-COOCH2CH3), 15.1 (-CH2OCH2CH3), 60.9 (-COOCH2CH3), 65.9 (-
20 CH2OCH2CH3), 68.0 (-COOCH2CH2-), 71.2 (-COOCH2CH2-), 120.1 (pyran-C-5), 120.3 (pyran-C-3), 152.3 (pyran-C-
21 6), 153.5 (pyran-C-2), 160.0 (-COOC2H5), 160.2 (-COOCH2CH2-), 178.0 (pyran-C-4). MS: m/z 284 (M+). Anal.
22 calcd. for C13H16O7: C, 54.93%; H, 5.67%. Found: C, 54.81%; H, 5.53%.
23 Reaction of compound 4a with diethylene glycol monomethyl ether (5c)
24 Diethyl chelidonate (4a) (0.53 g, 2.5 mmol) and diethylene glycol monomethyl ether (5c) (0.90 g, 7.5 mmol)
25 were reacted according to the general procedure. Compounds 6c and 7c were obtained.
26 Bis[2-(2-methoxyethoxy)ethyl] 4-oxo-4H-pyran-2,6-dicarboxylate (6c). Yellow oil (0.70 g, 72%, Rf = 0.70). IR
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27 (KBr, νmax, cm-1): 2985, 2883, 1755, 1660, 1623, 1598, 1456, 1275, 1248, 1109, 956, 862, 779. H NMR (400
28 MHz, CDCl3): δH 3.38 (6H, s, CH3O-), 3.51-3.56 (4H, m, -CH2CH2OCH3), 3.68-3.71 (4H, m, -CH2CH2OCH3), 3.80-
29 3.85 (4H, m, -COOCH2OCH2-), 4.52-4.55 (4H, m, -COOCH2-), 7.18 (2H, s, pyran-CH-3, -5). 13C NMR (100 MHz,
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