FULL PAPERS
Synthesis of Benzofurans
(m, 1H), 7.43–7.46 (m, 2H), 9.36 ppm (s, 1H); 13C NMR
(100 Hz, DMSO, 258C): d=64.7, 104.2, 108.7, 111.7, 113.4,
115.9, 116.2, 120.2, 121.7, 125.9, 129.9, 147.2, 149.0, 153.6,
153.9 ppm; IR: v=3173, 2918, 2878, 2659, 1925, 1889, 1847,
1775, 1684, 1644, 1616, 1598, 1498, 1465, 1443, 1383, 1302,
1231, 1186, 1138, 1088, 1033, 985, 957, 925, 799, 745, 610,
452 cmÀ1; HRMS (EI): m/z: calcd for C15H10NaO3: 261.0528
[M + Na]+; found: 261.0522.
1H); 13C NMR (100 Hz, DMSO, 258C): d=28.8, 71.4, 99.7,
105.1, 109.4, 111.0, 112.4, 121.6, 122.7, 124.9, 128.4, 130.0,
148.2, 153.5, 156.2, 160.3 ppm; IR: v=3293, 3003, 2962,
2921, 2842, 1605, 1510, 1466, 1415, 1302, 1244, 1193, 1090,
1034, 933, 837, 801, 771, 670, 564, 521, 438 cmÀ1; HRMS
+
(EI): m/z: calcd for C16H14NaO2: 277.0841 [M + Na]
;
found: 277.0846.
2-(4-(Benzyloxy)phenyl)benzofuran-5-ol (3r): Dark gery
6,7,8,9-Tetrahydrodibenzo[b,d]furan-2-ol (3l):[26a] Dark
grey solid, mp: 102–1038C; 1H NMR (400 Hz, DMSO,
258C): d=1.71–1.79 (m, 2H), 1.82–1.88 (m, 2H), 2.49–2.52
(m, 2H), 2.64–2.67 (m, 2H), 6.65 (dd, J=2.4, 8.8 Hz, 1H),
6.76 (d, J=2.4 Hz, 1H), 7.24 (d, J=8.8 Hz, 1H), 9.08 ppm
(s, 1H); 13C NMR (100 Hz, DMSO, 258C): d=19.9, 22.2,
22.5, 23.0, 103.4, 110.7, 111.3, 112.3, 129.1, 147.7, 153.0,
154.2 ppm.
solid, mp: 152–1548C; H NMR (400 MHz, DMSO, 258C):
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d=5.16 (s, 2H), 6.71 (dd, J=2.4, 8.4 Hz, 1H), 6.91 (d, J=
2.4 Hz, 1H), 7.11–7.14 (m, 3H), 7.34–7.42 (m, 4H), 7.46-
7.48 (m, 2H), 7.80 (d, J=8.8 Hz, 2H), 9.17 ppm (s, 1H);
13C NMR (100 MHz, DMSO, 258C): d=69.4, 100.3, 105.2,
111.0, 112.7, 115.3, 122.9, 126.1, 127.8, 127.9, 128.5, 129.9,
136.8, 148.3, 153.5, 155.7, 158.7 ppm; IR: v=3443, 3224,
2922, 2854, 1725, 1607, 1567, 1505, 1462, 1379, 1301, 1248,
1206, 1175, 1141, 1112, 1005, 917, 834, 796, 746, 698, 664,
616, 522, 449 cmÀ1; HRMS (EI): m/z: calcd for C21H16NaO3:
339.0997 [M + Na]+; found: 339.0992.
7,8,9,10-Tetrahydro-6H-cyclohepta[b]benzofuran-2-ol
(3m): Dark grey solid, mp: 98–998C; 1H NMR (400 HZ,
DMSO, 258C): d=1.68–1.77 (m, 6H), 2.54–2.56 (m, 2H),
2.79–2.82 (m, 2H), 6.63 (dd, J=2.4, 8.8 Hz, 1H), 6.76 (d, J=
2.0 Hz, 1H), 7.18 (d, J=8.8 Hz, 1H), 9.04 ppm (s, 1H);
13C NMR (100 Hz, DMSO, 258C): d=22.6, 25.9, 27.9, 28.6,
29.9, 103.2, 110.5, 111.4, 115.4, 130.8, 146.7, 153.0,
156.5 ppm; IR: v=3240, 2919, 2848, 2682, 1829, 1711, 1614,
1593, 1459, 1408, 1364, 1297, 1248, 1194, 1148, 1088, 1040,
956, 858, 822, 800, 773, 696, 512, 433 cmÀ1; HRMS (EI): m/z:
calcd for C13H14NaO2: 225.0891 [M + Na]+; found: 225.0896.
6,7,8,9,10,11-Hexahydrocycloocta[b]benzofuran-2-ol (3n):
2’,3’-Dihydro-[2,5’-bibenzofuran]-5-ol (3s): Light grey
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solid, mp: 165–1678C; H NMR (400 Hz, DMSO, 258C): d=
3.24 (t, J=8.8 Hz, 2H), 4.58 (t, J=8.8 Hz, 2H), 6.69 (dd, J=
2.4, 8.8 Hz, 1H), 6.86 (d, J=8.4 Hz, 1H), 6.89 (d, J=2.4 Hz,
1H), 7.05 (s, 1H), 7.34 (d, J=8.8 Hz, 1H), 7.61 (dd, J=1.6,
8.4 Hz, 1H), 7.73 (s, 1H), 9.16 ppm (s, 1H); 13C NMR
(100 Hz, DMSO, 258C): d=28.8, 71.4, 99.7, 105.1, 109.4,
111.0, 112.4, 121.6, 122.7, 124.9, 128.4, 130.0, 148.2, 153.5,
156.2, 160.3 ppm; IR: v=3421, 3109, 2962, 2893, 2854, 1612,
1597, 1473, 1421, 1372, 1336, 1300, 1279, 1241, 1199, 1151,
1125, 1107, 1033, 980, 942, 891, 854, 820, 793, 737,557,
438 cmÀ1; HRMS (EI): m/z: calcd for C16H12NaO3: 275.0648
[M + Na]+; found: 275.0640.
1
Light grey solid, mp: 119–1218C; H NMR (400 Hz, DMSO,
258C): d=1.41–1.43 (m, 4H), 1.64–1.76 (m, 4H), 2.65–2.68
(m, 2H), 2.80–2.84 (m, 2H), 6.63 (dd, J=2.4, 8.4 Hz, 1H),
6.76 (d, J=2.4 H z, 1H), 7.20 (d, J=8.8 Hz, 1H), 9.03 ppm
(s, 1H); 13C NMR (100 Hz, DMSO, 258C): d=20.8, 25.1,
25.5, 25.7, 26.9, 27.7, 103.1, 110.6, 111.4, 113.2, 130.2, 147.2,
152.9, 155.0 ppm; IR: v=3284, 2926, 2851, 2686, 1834, 1711,
1594, 1459, 1401, 1352, 1301, 1193, 1124, 940, 856, 800, 743,
697, 432 cmÀ1; HRMS (EI): m/z: calcd for C14H16NaO2:
239.1048 [M + Na]+; found: 239.1041.
2-(Benzo[d][1,3]dioxol-5-yl)benzofuran-5-ol (3t): Dark
grey solid, mp: 175–1768C; 1H NMR (400 Hz, DMSO,
258C): d=6.08 (s, 2H), 6.72 (dd, J=2.4, 8.8 Hz, 1H), 6.90
(d, J=2.4 Hz, 1H), 7.02 (d, J=8.0 Hz, 1H), 7.14 (s,1H),
7.35–7.42 (m, 3H), 9.20 ppm (s, 1H); 13C NMR (100 Hz,
DMSO, 258C): d=100.8, 101.4, 104.9, 105.2, 108.8, 111.1,
112.9, 118.7, 124.2, 129.8, 147.8, 148.0, 148.2, 153.5,
155.5 ppm; IR: v=3421, 3257, 3111, 2898, 1600, 1542, 1501,
1474, 1363, 1256, 1203, 1151, 1102, 1040, 936, 862, 816, 797,
Ethyl
8-hydroxy-1,2,3,4-tetrahydrodibenzo[b,d]furan-2-
carboxylate (3o): Grey solid, mp: 102–1038C; 1H NMR
(400 Hz, DMSO, 258C): d=1.19–1.23 (m, 3H), 1.88–1.99
(m, 1H), 2.18–2.20 (m, 1H), 2.64–2.85 (m, 5H), 4.08–4.16
(m, 2H), 6.64 (dd, J=2.4, 8.8 Hz, 1H), 6.77 (d, J=2.4 Hz,
1H), 7.23 (d, J=8.4 Hz, 1H), 9.09 ppm (s, 1H); 13C NMR
(100 Hz, DMSO, 258C): d=14.1, 21.9, 22.6, 25.1, 28.1, 38.6,
103.5, 110.9, 111.0, 111.6, 128.7, 148.0, 153.1, 153.4,
174.2 ppm; IR: v=3379, 2983, 2907, 2849, 1848, 1698, 1612,
1574, 1466, 1411, 1378, 1326, 1293, 1223, 1187, 1123, 1026,
854, 812, 723, 631, 479 cmÀ1; HRMS (EI): m/z: calcd for
739, 675, 585, 445 cmÀ1
; HRMS (EI): m/z: calcd for
C15H10NaO4: 277.0477 [M + Na]+; found: 277.0471.
2-(Furan-2-yl)benzofuran-5-ol (3u):[8] Dark grey solid,
1
mp: 149–1508C; H NMR (400 Hz, DMSO, 258C): d=6.66–
6.67 (m, 1H), 6.75 (dd, J=2.4, 8.8 Hz, 1H), 6.91 (d, J=
3.6 Hz, 1H), 6.94 (d, J=2.4 Hz, 1H), 6.99 (s, 1H), 7.38 (d,
J=8.8 Hz, 1H), 7.84 (d, J=1.2 Hz, 1H), 9.27 ppm (s, 1H);
13C NMR (100 Hz, DMSO, 258C): d=101.3, 105.5, 108.0,
111.3, 112.1, 113.4, 129.1, 144.0, 145.3, 147.8, 148.1,
153.7 ppm.
+
C15H16NaO4: 283.0946 [M + Na] ; found: 283.0941.
2-(4-Methoxyphenyl)benzofuran-5-ol (3p):[37] Light yellow
1
solid, mp: 190–1918C; H NMR (400 Hz, DMSO, 258C): d=
2-(Thiophen-2-yl)benzofuran-5-ol (3v):[8] Dark grey solid,
1
3.80 (s, 3H), 6.71 (dd, J=2.4, 8.4 Hz, 1H), 6.91(d, J=2.4 Hz,
1H), 7.04 (d, J=8.8 Hz, 2H), 7.11 (s, 1H), 7.36 (d, J=
8.8 Hz, 1H), 7.80 (d, J=8.4 Hz, 2H), 9.20 ppm (s, 1H); 13C
(100 Hz, DMSO, 258C): d=55.3, 100.2, 105.2, 111.1, 112.6,
114.5, 122.7, 126.1, 129.9, 148.3, 153.5, 155.8, 159.7 ppm.
2-(4-Methoxyphenyl)-3-methylbenzofuran-5-ol (3q): Light
grey solid, mp: 140–1428C; 1H NMR (400 Hz, DMSO,
258C): d=2.33 (s, 3H), 3.81 (s, 3H), 6.74 (dd, J=2.4, 8.8 Hz,
1H), 6.89 (d, J=2.4 Hz, 1H), 7.07 (d, J=8.8 Hz, 2H), 7.33
(d, J=8.4 Hz, 1H), 7.69 (d, J=8.8 Hz, 2H), 9.20 ppm (s,
mp: 135–1368C; H NMR (400 Hz, DMSO, 258C): d=6.74
(dd, J=2.8, 8.8 Hz, 1H), 6.92 (d, J=2.4 Hz, 1H), 7.08 (s,
1H), 7.17–7.19 (m, 1H), 7.38 (d, J=8.8 Hz, 1H), 7.57–
7.58(m, 1H), 7.65–7.66 (m, 1H), 9.29 ppm (s, 1H); 13C NMR
(100 Hz, DMSO, 258C): d=101.4, 105.3, 111.2, 113.3, 125.0,
126.9, 128.4, 129.5, 132.4, 148.1, 151.1, 153.7 ppm.
[2,2’-Bibenzofuran]-5-ol (3w): Light grey solid, mp: 133–
1
1358C; H NMR (400 Hz, DMSO, 258C): d=6.85 (dd, J=
2.4, 8.8 Hz, 1H), 7.04 (d, J=2.4 Hz, 1H), 7.27–7.31 (m, 2H),
7.34–7.38 (m, 2H), 7.46 (d, J=8.8 Hz, 1H), 7.67 (dd, J=8.4,
Adv. Synth. Catal. 0000, 000, 0 – 0
ꢀ 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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