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New Journal of Chemistry
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21.8, 20.8, 15.5 ppm; HRMS (ESI-TOF) m/z: [M + Na]+ Calcd for (s, 1H), 2.75 (q, J = 7.6 Hz, 2H), 2.37 (s, 3H), 2.32 (s, 3H), 1.27 (t,
C18H16O5SNa 367.0611; Found 367.0611.
J = 7.7 Hz, 3H) ppm; C{1H} NMR (125 MDHOzI:,1C0D.10C3l39)/:C9N=J0166413.82A,
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5,8-Dimethyl-2-oxo-2H-chromen-4-yl-4-
158.2, 152.7, 150.0, 135.7, 133.8, 131.9, 129.2, 128.6, 126.1,
methylbenzenesulfonate (5i)
. Yield = 151.5 mg, 88%, white 120.4, 114.4, 103.3, 29.0, 20.8, 15.5, 14.8 ppm; HRMS (ESI-TOF)
solid, M.p. 146–148
C; IR (CHCl3): max = 2967, 1727, 1646, m/z: [M + Na]+ Calcd for C19H18O5SNa 381.0767; Found
1598, 1446, 1411, 1374, 1282, 1220, 1194, 1179, 1095, 1039, 381.0769.
1011, 971, 924, 876, 816, 695, 660, 566, 544 cm-1; 1H NMR (400 5,8-Dimethyl-2-oxo-2H-chromen-4-yl
4-
MHz, CDCl3):
7.25 (d, J = 7.6 Hz, 1H), 6.91 (d, J = 7.6 Hz, 1H), 6.27 (s, 1H), 2.53 M.p. 152–154
(s, 3H), 2.46 (s, 3H), 2.33 (s, 3H) ppm; 13C{1H} NMR (100 MHz, 1201, 1167, 1129, 1088, 1005, 975, 921, 845, 814, 763, 734, 669,
CDCl3): = 7.89 (d, J = 8.4 Hz,
= 160.6, 159.9, 153.0, 146.8, 133.7, 133.5, 132.0, 580, 548 cm-1; 1H NMR (400 MHz, CDCl3):
= 7.88 (d, J = 8.4 Hz, 2H), 7.39 (d, J = 8.0 Hz, 2H), ethylbenzenesulfonate (7i). Yield = 148.6 mg, 83%, white solid;
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C; IR (CHCl3): max = 1732, 1630, 1593, 1377,
130.4, 128.4, 127.7, 124.4, 113.2, 102.4, 22.8, 21.7, 15.7 ppm; 2H), 7.40 (d, J = 8.4 Hz, 2H), 7.20 (d, J = 7.6 Hz, 1H), 6.88 (d, J =
HRMS (ESI-TOF) m/z: [M + Na]+ Calcd for C18H16O5SNa 367.0611; 7.6 Hz, 1H), 6.27 (s, 1H), 2.73 (q, J = 7.6 Hz, 2H), 2.50 (s, 3H), 2.30
Found 367.0611.
6-Methyl-2-oxo-2H-chromen-4-yl
(s, 3H), 1.25 (t, J = 7.7 Hz, 3H) ppm; 13C{1H} NMR (100 MHz,
4-ethylbenzenesulfonate CDCl3): = 160.5, 159.7, 152.8, 152.7, 133.5, 133.4, 132.0,
(7a). Yield = 146.4 mg, 85%, white solid, M.p. 96–98 oC; IR 129.1, 128.4, 127.6, 124.2, 113.0, 102.2, 28.8, 22.7, 15.6, 14.6
(CHCl3):
1317, 1276, 1203, 1169, 1131, 1062, 923, 833, 792, 744, 705, 381.0767; Found 381.0769.
659, 603, 573, 541 cm-1; 1H NMR (500 MHz, CDCl3): = 7.91 (d, 6-Methyl-2-oxo-2H-chromen-4-yl benzenesulfonate (8a).16g
J = 8.1 Hz, 2H), 7.41 (d, J = 8.4 Hz, 2H), 7.38–7.31 (m, 2H), 7.18 Yield = 123.4 mg, 78%, white solid, M.p. 140–142
C, lit.16g M.p.
C; IR (CHCl3): max = 3127, 1730, 1629, 1578, 1450,
max = 2972, 1732, 1631, 1578, 1491, 1425, 1388, 1365, ppm; HRMS (ESI-TOF) m/z: [M + Na]+ Calcd for C19H18O5SNa
(d, J = 8.1 Hz, 1H), 6.27 (s, 1H), 2.74 (q, J = 7.6 Hz, 2H), 2.35 (s, 139–141
3H), 1.26 (t, J = 8.1 Hz, 3H) ppm; 13C{1H} NMR (125 MHz, CDCl3): 1425, 1382, 1364, 1316, 1203, 1168, 1063, 935, 922, 860, 820,
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= 161.0, 157.8, 152.8, 151.6, 134.4, 134.2, 131.8, 129.2, 128.5, 776, 759, 748, 684, 606, 586, 566 cm-1; H NMR (400 MHz,
122.7, 116.6, 114.5, 103.5, 28.9, 20.8, 14.8 ppm; HRMS (ESI- CDCl3): δ = 8.02 (d, J = 8.2Hz, 2H), 7.74 (dt, J = 7.3, 1.2 Hz, 1H),
TOF) m/z: [M + Na]+ Calcd for C18H16O5SNa 367.0611; Found 7.64–7.59 (m, 2H), 7.40–7.39 (m, 2H), 7.20 (d, J = 8.6 Hz, 1H),
367.0605.
2-Oxo-2H-chromen-4-yl 4-ethylbenzenesulfonate (7b). Yield = 160.9, 157.8, 151.7, 135.3, 134.8, 134.5, 134.3, 129.8, 128.4,
6.27 (s, 1H), 2.36 (s, 3H) ppm; 13C{H} NMR (100 MHz, CDCl3): δ =
137.1 mg, 83%, brown semi-solid; IR (CHCl3): max = 2969, 2932, 122.7, 116.7, 114.5, 103.8, 20.8 ppm; HRMS (ESI-TOF) m/z: [M
2874, 1732, 1626, 1608, 1569, 1490, 1452, 1372, 1327, 1274, + Na]+ Calcd for C16H12O5SNa 339.0298; Found 339.0299.
16g
1197, 1176, 1132, 1067, 1032, 933, 875, 837, 790, 753, 719, 658, 2-Oxo-2H-chromen-4-yl benzenesulfonate, (8b)
602, 577, 546 cm-1; 1H NMR (400 MHz, CDCl3):
= 7.95 (d, J = 8.1 110.3 mg, 73%, white solid, M.p. 116 120
Hz, 2H), 7.66 (t, J = 8.4 Hz, 1H), 7.63 (t, J = 8.1 Hz, 1H), 7.42 (d, J 118 120 C; IR (CHCl3): max = 3075, 1736, 1625, 1606, 1567,
.
Yield =
−
C, lit.16g M.p.
−
= 8.0 Hz, 2H), 7.37–7.21 (m, 2H), 6.36 (s, 1H), 2.78 (q, J = 7.7 Hz, 1450, 1386, 1373, 1278, 1177, 1128, 1092, 1071, 1031, 936,
2H), 1.30 (t, J = 7.8 Hz, 3H) ppm; 13C{1H} NMR (100 MHz, CDCl3): 910, 877, 855, 767, 720, 683, 606, 588, 568, 538 cm-1; 1H NMR
= 160.8, 157.8, 153.4, 152.9, 133.2, 131.8, 129.2, 128.5, 124.5, (500 MHz, CDCl3): = 8.03 (d, J = 8.3 Hz, 2H), 7.75 (t, J = 7.5 Hz,
123.1, 116.9, 114.9, 103.6, 28.9, 14.8 ppm; HRMS (ESI-TOF) m/z: 1H), 7.66–7.59 (m, 3H), 7.59–7.55 (m, 1H), 7.32 (d, J = 8.2 Hz,
[M + H]+ Calcd for C17H15O5S 331.0635; Found 331.0632.
6-(tert-Butyl)-2-oxo-2H-chromen-4-yl-4-
1H), 7.29–7.24 (m, 1H), 6.33 (s, 1H) ppm; 13C{1H} NMR (125
MHz, CDCl3): = 160.7, 157.7, 153.5, 135.4, 134.8, 133.3, 129.8,
ethylbenzenesulfonate (7c). Yield = 158.5 mg, 82%, white semi 128.4, 124.5, 123.1, 117.0, 114.9, 103.9 ppm; HRMS (ESI-TOF)
solid; IR (CHCl3): max = 3101, 2967, 2871, 1735, 1630, 1597, m/z: [M + Na]+ Calcd for C15H10O5SNa 325.0141; Found
1577, 1491, 1461, 1427, 1390, 1371, 1354, 1315, 1263, 1208, 325.0143.
1178, 1143, 1111, 1093, 1060, 935, 909, 859, 842, 791, 762, 744, 6-(tert-Butyl)-2-oxo-2H-chromen-4-yl benzenesulfonate (8c).
720, 679, 658, 599, 550 cm-1; 1H NMR (500 MHz, CDCl3):
= 7.89 Yield = 136.2 mg, 76%, brown semi solid; IR (CHCl3): max = 2967,
(d, J = 8.2 Hz, 2H), 7.58 (dd, J = 8.5, 2.4 Hz, 1H), 7.48 (d, J = 2.3 2905, 1736, 1630, 1577, 1449, 1427, 1393, 1372, 1315, 1263,
Hz, 1H), 7.39 (d, J = 8.3 Hz, 2H), 7.23 (d, J = 8.6 Hz, 1H), 6.32 (s, 1203, 1185, 1143, 1092, 1060, 935, 909, 863, 843, 769, 722, 685,
1H), 2.73 (q, J = 7.6 Hz, 2H), 1.27 (s, 9H), 1.24 (t, J = 7.5 Hz, 3H) 603, 575, 550 cm-1; 1H NMR (500 MHz, CDCl3):
= 8.00 (d, J = 8.1
= 161.0, 158.1, 152.7, Hz, 2H), 7.73 (t, J = 7.2 Hz, 1H), 7.62–7.55 (m, 3H), 7.46 (d, J =
151.5, 147.7, 132.0, 130.9, 129.2, 128.4, 119.1, 116.5, 114.2, 1.4 Hz, 1H), 7.22 (d, J = 8.3 Hz, 1H), 6.32 (s, 1H), 1.25 (s, 9H) ppm;
ppm; 13C{1H} NMR (125 MHz, CDCl3):
104.4, 34.6, 31.1, 28.9, 14.8 ppm; HRMS (ESI-TOF) m/z: [M + 13C{1H} NMR (125 MHz, CDCl3):
= 160.8, 157.9, 151.5, 147.7,
Na]+ Calcd for C21H22O5SNa 409.1080; Found 409.1077.
135.2, 134.8, 130.9, 129.7, 128.2, 119.0, 116.4, 114.1, 104.4,
6,8-Dimethyl-2-oxo-2H-chromen-4-yl
4- 34.5, 31.1 ppm; HRMS (ESI-TOF) m/z: [M + Na]+ Calcd for
ethylbenzenesulfonate (7f). Yield = 147 mg, 82%, white semi- C19H18O5SNa 381.0767; Found 381.0768.
solid; IR (CHCl3): max = 3106, 2970, 2928, 2877, 1732, 1631, 2-Oxo-6-phenyl-2H-chromen-4-yl benzenesulfonate (8d). Yield
1596, 1578, 1491, 1413, 1391, 1366, 1317, 1276, 1202, 1169, = 128.7 mg, 68%, brown semi solid; IR (CHCl3): max = 2979,
1131, 1093, 1061, 923, 859, 833, 792, 760, 745, 706, 681, 659, 2932, 1732, 1626, 1576, 1467, 1376, 1277, 1199, 1168, 1090,
618, 602, 573, 542 cm-1; 1H NMR (500 MHz, CDCl3): = 7.91 (d, 1050, 985, 922, 911, 790, 758, 733, 666, 548 cm-1; 1H NMR (500
J = 8.1 Hz, 2H), 7.41 (d, J = 7.9 Hz, 2H), 7.25–7.19 (m, 2H), 6.25 MHz, CDCl3):
= 8.04 (d, J = 8.2 Hz, 2H), 7.90–7.69 (m, 3H),
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J. Name., 2013, 00, 1-3 | 7
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