The Journal of Organic Chemistry
-(3,5-Dichlorophenyl)-2H-pyran-4(3H)-one (9n):
Page 12 of 19
6
1507, 1462, 1412, 1346, 1283, 1263, 1238, 1189, 1122,
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-1
Reaction time = 5.5 h, brown solid (224 mg, 92%), M.p.
1078, 1051, 1017, 985, 886, 852, 842, 780, 670, 537 cm .
1
+
8
2−84 C. H NMR (500 MHz, CDCl
3
): δ = 2.67 (t, J = 6.6 Hz,
HRMS (ESI-TOF) m/z: [M + Na] Calcd for C16
H
14
4
O Na
2
H), 4.67 (t, J = 6.6 Hz, 2H), 5.97 (s, 1H), 7.46 (s, 1H), 7.59 (d,
293.0784; Found 293.0785.
6-(Thiophen-2-yl)-2H-pyran-4(3H)-one (9t): Reaction
time = 5 h, yellow semi-solid (162.2 mg, 90%). H NMR (400
13
1
J = 1.0 Hz, 2H) ppm. C{ H} NMR (125 MHz, CDCl
8.5, 103.6, 124.8, 131.2, 135.5, 135.7, 167.4, 192.1 ppm. IR
CHCl ): max = 3083, 2922, 2854, 1673, 1599, 1583, 1562,
3
): δ = 36.0,
1
6
(
3
MHz, CDCl
3
): δ = 2.64 (t, J = 6.7 Hz, 2H), 4.63 (t, J = 6.7 Hz,
1
1
463, 1440, 1420, 1391, 1345, 1241, 1188, 1122, 1080,
2H), 5.93 (s, 1H), 7.11 (dd, J = 5.0, 3.9 Hz, 1H), 7.51‒7.54 (m,
-1
13
1
016, 981, 885, 860, 801, 758 cm . HRMS (ESI-TOF) m/z:
2H) ppm. C{ H} NMR (125 MHz, CDCl
101.3, 128.2, 128.7, 130.5, 136.4, 165.6, 192.0 ppm. IR
(CHCl ): max = 2925, 2851, 1658, 1581, 1463, 1422, 1398,
1366, 1344, 1229, 1186, 1072, 1039, 984, 885, 859, 821,
3
): δ = 36.1, 68.4,
+
[
M + H] Calcd for C11
H
9
O
2
2
Cl 242.9974; Found 242.9977.
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
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6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
6
-(4-Chlorophenyl)-2H-pyran-4(3H)-one (9o): Reaction
3
1
time = 5 h, white solid (200.3 mg, 96%), M.p. 76−78 C. H
NMR (400 MHz, CDCl
=
=
3
-1
+
3
): δ = 2.66 (t, J = 6.8 Hz, 2H), 4.66 (t, J
754, 715, 667 cm . HRMS (ESI-TOF) m/z: [M + H] Calcd for
S 181.0318; Found 181.0320.
6.8 Hz, 2H), 5.99 (s, 1H), 7.41 (d, J = 8.7 Hz, 2H), 7.66 (d, J
C
9
H
9
O
2
13
1
8.7, 2.2 Hz, 2H) ppm. C{ H} NMR (100 MHz, CDCl
3
): δ =
6-(Furan-2-yl0)-2H-pyran-4(3H)-one (9u): Reaction time
1
5.9, 68.3, 102.5, 127.8, 129.0, 131.1, 137.9, 169.3, 192.5
= 5 h, brown solid (151 mg, 92%), Mp = 84−86 C. H NMR
ppm. IR (CHCl
3
): max = 2939, 2864, 2844, 1663, 1599, 1454,
(400 MHz, CDCl
Hz, 2H), 5.94 (s, 1H), 6.51 (dd, J = 3.4, 1.7 Hz, 1H), 6.90 (d, J
3
): δ = 2.63 (t, J = 6.7 Hz, 2H), 4.59 (t, J = 6.7
-1
1
412, 1133, 1093, 1052, 1033, 771 cm . HRMS (ESI-TOF)
+
13
1
m/z: [M + Na] Calcd for C11
31.0181.
H
9
O
2
ClNa 231.0183; Found
= 3.4 Hz, 1H), 7.53 (d, J = 1.0 Hz, 1H) ppm. C{ H} NMR (125
MHz, CDCl ): δ = 36.2, 68.3, 100.9, 112.3, 113.6, 145.6, 147.2,
161.4, 191.8 ppm. IR (CHCl ): max = 3123, 3105, 2970, 1647,
2
3
6
-(3-Bromophenyl)-2H-pyran-4(3H)-one (9p): Reaction
3
1
time = 5 h, yellow oil (228 mg, 90%). H NMR (400 MHz,
1617, 1540, 1472, 1425, 1357, 1269, 1255, 1228, 1186,
1089, 1062, 1001, 984, 923, 882, 825, 814, 664, 596 cm .
HRMS (ESI-TOF) m/z: [M + Na] Calcd for C
187.0366; Found 187.0365.
6-Heptadecyl-2H-pyran-4(3H)-one (9v): Reaction time = 7
h, white solid (296.2 mg, 88%), Mp = 38−40 C. H NMR (500
-1
CDCl
3
): δ = 2.66 (t, J = 6.7 Hz, 2H), 4.66 (t, J = 6.8 Hz, 2H), 5.98
+
(
s, 1H), 7.30 (t, J = 7.9 Hz, 1H), 7.59‒7.64 (m, 2H), 7.88 (t, J =
9
H
8
3
O Na
.7 Hz, 1H) ppm. 13C{ H} NMR (125 MHz, CDCl
1
): δ = 36.0,
1
6
1
1
3
8.4, 103.0, 122.9, 125.0, 129.5, 130.2, 134.5, 134.7, 168.8,
92.4 ppm. IR (CHCl
411, 1033, 771 cm . HRMS (ESI-TOF) m/z: [M + Na] Calcd
1
3
): max = 2938, 2829, 2523, 1655, 1560,
-1
+
MHz, CDCl
3
): δ = 0.86 (t, J = 6.9 Hz, 3H), 1.24‒1.27 (m, 28H),
for C11
H
9
2
O BrNa 274.9678; Found 274.9677.
1.53 (quin, J = 7.4 Hz, 2H), 2.21 (t, J = 7.6 Hz, 2H), 2.50 (t, J =
13
1
(E)-6-Styryl-2H-pyran-4(3H)-one (9q): Reaction time = 5
6.8 Hz, 2H), 4.43 (t, J = 6.8 Hz, 2H), 5.32 (s, 1H) ppm. C{ H}
NMR (125 MHz, CDCl ): δ = 14.1, 22.7, 26.3, 29.1, 29.3, 29.4,
29.5, 29.6, 29.64, 29.66, 29.7, 31.9, 34.8, 35.7, 67.9, 104.5,
178.2, 192.4 ppm. IR (CHCl ): max = 2925, 2853, 1668, 1606,
1465, 1403, 1360, 1252, 1232, 1195, 1156, 1071, 1033, 983,
1
h, yellow solid (188.2 mg, 94%), M.p. 104−106 C. H NMR
3
(
500 MHz, CDCl
3
): δ = 2.63 (t, J = 6.7 Hz, 2H), 4.58 (t, J = 6.7
Hz, 2H), 5.55 (s, 1H), 6.74 (d, J = 15.9 Hz, 1H), 7.35‒7.40 (m,
3
H), 7.49‒7.51 (m, 2H) ppm. 13C{ H} NMR (125 MHz, CDCl
1
):
4
3
-1
+
δ = 36.1, 67.9, 106.4, 121.4, 127.7, 128.9, 129.7, 135.1, 137.4,
875, 821, 722, 666 cm . HRMS (ESI-TOF) m/z: [M + Na]
Calcd for C22 Na 359.2921; Found 359.2915.
1
1
1
68.8, 192.7 ppm. IR (CHCl
579, 1565, 1464, 1449, 1404, 1463, 1329, 1241, 1190,
124, 1075, 1038, 1011, 984, 817, 737, 695 cm . HRMS
3
): max = 2918, 2849, 1653, 1625,
H
40
O
2
6-Hexyl-2H-pyran-4(3H)-one (9w): Reaction time = 3 h,
yellow oil (133 g, 73%). H NMR (400 MHz, CDCl
-1
1
3
): δ = 0.88
+
(
ESI-TOF) m/z: [M + Na] Calcd for C13
H
12
O
2
Na 223.0730;
(t, J = 6.2 Hz, 3H), 1.25‒1.29 (m, 6H), 1.51‒1.60 (m, 2H), 2.23
(t, J = 7.5 Hz, 2H), 2.51 (t, J = 6.8 Hz, 2H), 4.44 (t, J = 6.8 Hz,
2H), 5.33 (s, 1H) ppm. C{ H} NMR (100 MHz, CDCl
14.0, 22.5, 26.3, 28.7, 31.4, 34.8, 35.7, 67.9, 104.5, 178.2,
192.4 ppm. IR (CHCl ): max = 3012, 2957, 2927, 2856, 1666,
Found 223.0728.
13
1
(E)-6-(4-Methoxystyryl)-2H-pyran-4(3H)-one
(9r):
3
): δ =
Reaction time = 1 h, brown solid (221 mg, 96%), M.p.
1
1
18−120 C. H NMR (500 MHz, CDCl
3
): δ = 2.62 (t, J = 6.5
3
Hz, 2H), 3.84 (s, 3H), 4.56 (t, J = 6.5 Hz, 2H), 5.51 (s, 1H), 6.41
1604, 1464, 1403, 1362, 1252, 1232, 1197, 1159, 1071,
-1
+
(
d, J = 15.8 Hz, 1H), 6.90 (d, J = 8.5 Hz, 2H), 7.32 (d, J = 15.8
1035, 984, 822, 666 cm . HRMS (ESI-TOF) m/z: [M + Na]
Calcd for C11 Na 205.1199; Found 205.1196.
6-(4-Chlorophenyl)-2-pentyl-2H-pyran-4(3H)-one
13
1
Hz, 1H), 7.45 (d, J = 8.5 Hz, 2H) ppm. C{ H} NMR (125 MHz,
CDCl ): δ = 36.1, 55.4, 67.9, 105.8, 114.1, 119.1, 127.9, 129.3,
37.2, 161.0, 169.3, 192.7 ppm. IR (CHCl ): max = 3019,
H
18
O
2
3
(9x):
1
2
1
3
Reaction time = 15 h, pale yellow semi-solid (267.6 mg,
1
975, 2935, 1653, 1625, 1603, 1577, 1564, 1511, 1464,
421, 1361, 1174, 1075, 1033, 983, 970, 928, 669 cm .
96%). H NMR (500 MHz, CDCl
3
): δ = 0.92 (t, J = 7.0 Hz, 3H),
-1
1.33‒1.40 (m, 4H), 1.47‒1.53 (m, 1H), 1.57‒1.62 (m, 1H),
1.72‒1.89 (m, 1H), 1.91‒1.98 (m, 1H), 2.47‒2.58 (m, 2H),
4.50‒4.56 (m, 1H), 5.95 (s, 1H), 7.39 (d, J = 8.6 Hz, 2H), 7.65
(t, J = 8.6 Hz, 2H) ppm. C{ H} NMR (125 MHz, CDCl
13.9, 22.5, 24.7, 31.5, 34.4, 41.3, 79.7, 102.1, 127.7, 128.9,
131.3, 137.7, 169.0, 193.3 ppm. IR (CHCl ): max = 2955,
+
HRMS (ESI-TOF) m/z: [M + Na] Calcd for C14
H
14
3
O Na
2
53.0835; Found 253.0837.
,6'-(1,4-phenylene)bis(2H-pyran-4(3H)-one)
13
1
6
(9s):
1
3
): δ =
Reaction time = 10 h, yellow semi-solid (219 mg, 81%). H
NMR (500 MHz, CDCl
6.8 Hz, 4H), 6.08 (s, 2H), 7.79 (s, 4H) ppm. 13C{ H} NMR
125 MHz, CDCl ): δ = 35.9, 68.3, 103.2, 126.7, 135.4, 169.2,
92.7 ppm. IR (CHCl ): max = 2945, 2922, 2850, 1660, 1588,
3
): δ = 2.68 (t, J = 6.7 Hz, 4H), 4.68 (t, J
3
1
=
(
1
2931, 2860, 1663, 1600, 1564, 1489, 1467, 1409, 1380,
1334, 1299, 1276, 1092, 1052, 908, 840 cm . HRMS (ESI-
-1
3
3
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