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BENFERRAH et al.
with saturated NaCl solution and dried over MgSO4.
The solid product was recrystallized from ethanol (0.5 g).
148 (14), 77 (19), 69 (22), 57 (24), 43 (15). C15H12O5.
M 272.16 g/mol.
3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one
[DHA] (I). White solid recrystallized from ethyl
acetate, yield 80%, mp 108–110°C ([27]). IR spectrum,
ν, cm–1: 1710 (νC=O, cycle), 1610 (νC=O), 1570 (νC=C),
1186 (νOCO). TLC (pentane : ethyl acetate = 80 : 20).
UV-Vis (EtOH), λ, nm (log ε): 303 (3.23), 228 (3.27).
1Н NMR spectrum, δ, ppm: 2.26 s (3H, CH3), 2.66 s
(3H, CH3), 5.92 s (CH). 13С NMR spectrum, δ, ppm:
20.71, 29.97, 99.94, 101.19, 161.17, 169.40, 181.24,
6-(4-Chlorostyryl)-4-methoxy-2H-pyran-2-one
(IVb) synthesized from parachlorobenzaldehyde
(5 mmol, 0.7 g), MW power 40 W, time 7 min. The
yellow solid product was recrystallized from methanol,
yield 82%, mp 144°C ([40]). IR spectrum, ν, cm–1:
1
1720 (νC=O), 1648, 1554, 1256. Н NMR spectrum, δ,
ppm: 3.83 s (3H), 5.50 d, 5.95 d, 6.55 d, 7.32–7.48 m
(5H), 13С NMR spectrum, δ, ppm: 55.91, 89.06,
101.73, 119.18, 128.51, 129.10, 133.74, 134.37,
135.22, 158.26, 163.89, 170.9. MS m/z, %: 262 [M+].
C14H11ClO3. M 262.04 g/mol.
205.25. MS, m/z, %: 169 [M+, 100]. C8H8O4.
M
168.15 g/mol.
4-Hyroxy-6-methyl-2H-pyran-2-one [TAL] (II).
White solid recrystallized from water, yield 85%, mp
186–188°C ([27]). IR spectrum, ν, cm–1: 3320 (νOH),
1721 (νC=O), 1626 (νC=C), 1540, 1303, 1250 (νCOC),
870, 813. TLC (pentane : ethyl acetate = 80 : 20). UV-
Vis (EtOH), λ, nm (log ε): 390 (3.38), 278 (3.45), 215
(3.30). 1Н NMR spectrum, δ, ppm: 2.15 s (3H, CH3),
5.21 s (H3), 5.95 s (H5). 13С NMR spectrum, δ, ppm:
19.58, 88.30, 100.32, 163.42, 164.07, 170.70. MS, m/z,
%: 126 [M+, 33]. C6H6O3. M 126.12 g/mol.
6-(4-Methoxystyryl)-4-methoxy-2H-pyran-2-one
(IVc) synthesized from paramethoxybenzaldehyde
(5 mmol, 0.675 g), MW power 40W, time 10 min. The
yellow solid product was recrystallized from methanol,
yield 86%, mp 157°C ([41]). IR spectrum, ν, cm–1:
2840 [ν(CH, OCH3)], 1728 (νC=O), 1645, 1607, 1576,
1512, 1456, 1251, 1158, 1003, 833, 676. 1Н NMR
spectrum, δ, ppm: 3.83 s (3H, OCH3), 3.85 s (3H,
OCH3), 5.49 d (H3), 5.89 d (H5), 6.46 d (H7), 6.72 d
(2H, Harom), 7.44–7.49 m (3H, Harom). 13С NMR
spectrum, δ, ppm: 55.30, 55.88, 88.35, 100.41, 114.36,
116.40, 127.89, 129.9, 135.37, 159.12, 160.77, 164.15,
171.22. MS m/z, %: 259 (6), 258 [M+, 20], 254 (45),
253 (100), 226 (9), 225 (26), 211 (12), 198 (12), 187
(45), 184 (34), 183 (45), 169 (5), 158 (10), 115 (11),
89 (5), 77 (8), 69 (7). C15H14O4. M 228.28 g/mol.
4-Methoxy-6-methyl-2H-pyran-2-one (III).
Yellow solid recrystallized from ether, yield 79%, mp
86°C ([39]). IR spectrum, ν, cm–1: 1731, 1718 (νC=O),
1646 (νC=C), 1462, 1401, 1145 (νCOC), 940, 542. TLC
(pentane : ethyl acetate = 80 : 20). 1Н NMR spectrum,
δ, ppm: 2.20 s (3H, CH3), 3.79 s (3H, CH3O), 5.40 d
(H3), 5.77 d (H5). 13С NMR spectrum, δ, ppm: 19.74,
55.73, 87.27, 100.28, 161.88, 164.98, 171.24. MS, m/z,
%: 140 [M+, 53], 132 (8.6), 125 (47), 113 (8), 112
(100), 69 (36), 59 (25), 53 (30), 43 (45). C7H8O3. M
140.15 g/mol.
6-[2-(3,4-Dimethoxyphenyl)ethenyl]-4-methoxy-
2H-pyran-2-one (IVd) synthesized from 3,4-dimeth-
oxybenzaldehyde (5 mmol, 0.8 g), MW power 40 W,
time 10 min. The yellow solid product was recrys-
tallized from methanol, yield 79%, mp 162–163°C. IR
spectrum, ν, cm–1: 2848 [ν(CH, OCH3)], 1718 (νC=O),
6-{2-(Benzo[d][1,3]dioxol-5-yl)ethenyl}-4-
methoxy-2H-pyran-2-one (IVa) synthesized from
piperonal (5 mmol, 0.75 g), MW power 60 W, time
6 min. The yellow solid product was recrystallized
from methanol, yield 93%, mp 238°C. IR spectrum, ν,
cm–1: 3076, 1720 (νC=O), 1634 (νC=C), 1608, 1553,
1496, 1450, 1412, 1258, 962, 924, 810, 684. 1Н NMR
spectrum, δ, ppm: 3.80 s (3H, OCH3), 5.46 d (H3), 5.89
d (H5), 5.97 s (2H, OCH2O), 6.42 d (H7), 6.81 d
(H2arom), 6.99 d (H6arom), 7.41 d (H8). 13С NMR spec-
trum, δ, ppm: 55.86, 88.50, 100.68, 101.44, 105.91,
108.63, 116.82, 123.52, 129.15, 133.62, 148.30,
148.90, 158.80, 164.04, 171. MS m/z, %: 274 (42), 273
(100), 272 [M+, 58], 201 (16), 190 (20), 197 (12), 195
(14), 185 (10), 183 (15), 181 (13), 179 (19), 165 (8),
1
1551, 1412, 1251, 1053, 843, 687. Н NMR spectrum,
δ, ppm: 3.79 s (3H, OCH3-C4), 3.88 s (3H, OCH3-C12),
3.90 s (3H, OCH3-C11), 5.44 d (H3), 5.88 d (H5), 6.43 d
(H7), 6.84 d (H13), 7.00 d (H10), 7.05 d (H14), 7.42 d
(H8). 13С NMR spectrum, δ, ppm: 55.80, 55.90, 88.40,
100.50, 109.30, 111.20, 116.50, 121.6, 128.2, 135.60,
149.2, 150.4, 158.90, 164.1, 171.2. MS, m/z, %: 288
[M+]. C16H16O5. M 288.29 g/mol.
6-[2-(3,4,5-Trimethoxyphenyl)ethenyl]-4-
methoxy-2H-pyran-2-one (IVe) synthesized from
3,4,5-trimethoxybenzaldehyde (5 mmol, 0.975 g), MW
power 40 W, time 10 min. The yellow solid product
was recrystallized from ethyl acetate, yield 90%, mp
201°C. IR spectrum, ν, cm–1: 2838 [ν(CH, OCH3)],
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 85 No. 8 2015