The Journal of Organic Chemistry
Page 10 of 13
1
2
3
4
5
6
7
8
o
1
3-Methyl-2,5-di-p-tolylfuran (3bb): White solid (64%, 83 mg), mp 98-99 C; H NMR (400
MHz, CDCl3): δ 7.51 (d, J = 8.0 Hz, 4H), 7.16-7.09 (m, 4H), 6.45 (s, 1H), 2.30 (s, 3H), 2.28 (s,
3H), 2.22 (s, 3H) ; 13C NMR (100 MHz, CDCl3): δ 151.7 , 148.2 137.0, 136.4 , 129.4, 129.3,
129.2, 128.3, 125.3, 125.0, 123.7, 117.9, 110.1, 21.4, 21.3, 12.2. Anal calcd. for C19H18O: C,
86.99; H, 6.92%; Found: C, 87.02; H, 6.88%.
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
1
3-Ethyl-2,5-diphenylfuran (3ca):10 Colorless oil (62%, 76 mg); H NMR (400 MHz, CDCl3): δ
7.70-7.64 (m, 4H), 7.41-7.33 (m, 4H), 7.26-7.21 (m, 2H), 6.65 (s, 1H), 2.71 (q, J = 7.6 Hz, 2H),
1.27 (t, J = 7.6 Hz, 3H); 13C NMR (100 MHz, CDCl3): δ 152.1,147.7, 131.9, 130.9, 128.8,
128.7, 128.5, 127.3, 126.9, 125.6, 125.5, 125.3, 123.8, 108.8, 19.4, 14.5.
1
3-Ethyl-2-phenyl-5-p-tolylfuran (3cb): Colorless oil (60%, 78 mg); H NMR (400 MHz,
CDCl3): δ 7.61 (d, J = 9.2 Hz, 2H), 7.54 (d, J = 8.4 Hz, 2H), 7.36-7.32 (m, 2H), 7.21-7.17 (m,
1H), 7.12 (d, J = 8.0 Hz, 2H), 6.55 (s, 1H), 2.66 (q, J = 7.6 Hz, 2H), 2.29 (s, 3H), 1.22 (t, J = 7.6
Hz, 3H); 13C NMR (100 MHz, CDCl3): δ 152.3, 147.3, 137.1, 131.9, 129.4, 128.6, 128.3, 126.8,
125.6, 125.5, 123.7, 108.0, 21.4, 19.4, 14.5. Anal calcd. for C19H18O: C, 86.99; H, 6.92%;
Found: C, 86.89; H, 6.97%.
1
2-Phenyl-5-p-tolylfuran (3da): Colorless oil (54%, 63 mg); H NMR (400 MHz, CDCl3): δ
7.67 (d, J = 9.2 Hz, 2H), 7.57 (d, J = 8.4 Hz, 2H), 7.34-7.30 (m, 2H), 7.20-7.16 (m, 1H), 7.14
(d, J = 8.0 Hz, 2H), 6.66 (d, J = 3.6 Hz, 1H), 6.60 (d, J = 3.6 Hz, 1H), 2.30 (s, 3H); 13C NMR
(100 MHz, CDCl3): δ 153.7, 153.1, 137.3, 131.0, 129.5, 128.8, 128.2, 127.3, 123.8, 123.7,
107.3, 106.6, 21.4. Anal calcd. for C17H14O: C, 87.15; H, 6.02%; Found: C, 87.16; H, 6.05%.
2-o-Tolyl-5-p-tolylfuran (3eb): Colorless oil (52%, 64 mg),1H NMR (400 MHz, CDCl3): δ
7.78 (d, J = 7.6 Hz, 1H), 7.63 (d, J = 8.0 Hz, 2H), 7.27-7.24 (m, 3H), 7.21 (d, J = 8.0 Hz, 2H),
6.70 (d, J = 3.6 Hz, 1H), 6.62 (d, J = 3.6 Hz, 1H), 2.56 (s, 3H), 2.37 (s, 3H); 13C NMR (100
MHz, CDCl3): δ 153.4, 152.8, 137.3, 134.5, 131.4, 130.3, 129.5, 128.3, 127.4, 126.9, 126.1,
123.8, 110.7, 106.3, 22.2, 21.4. Anal calcd. for C18H16O: C, 87.06; H, 6.49%; Found: C, 87.01;
H, 6.56%.
1
2-(4-(Methylthio)phenyl)-5-phenylfuran (3fa): Colorless oil (52%, 69 mg); H NMR (400
MHz, CDCl3): δ 7.72 (d, J = 9.2 Hz, 2H), 7.64 (d, J = 8.8 Hz, 2H), 7.38 (t, J = 8.0 Hz, 2H),
13
7.28-7.24 (m, 3H), 6.71 (d, J = 3.2 Hz, 1H), 6.67 (d, J = 3.6 Hz, 1H), 2.50 (s, 3H); C NMR
(100 MHz, CDCl3): δ 153.3, 153.1, 137.7, 130.8, 128.8, 127.9, 127.4, 126.9, 124.2, 123.8,
107.4, 107.0, 16.0. Anal calcd. for C17H14OS: C, 76.66; H, 5.30%; Found: C, 76.68; H, 5.34%.
1
2-(4-Methoxyphenyl)-5-(thiophen-2-yl)furan (3gc): Colorless oil (49%, 62 mg); H NMR
(400 MHz, CDCl3): δ 7.57 (d, J = 8.8 Hz, 2H), 7.21 (d, J = 4.4 Hz, 1H), 7.14 (d, J = 6.4 Hz,
ACS Paragon Plus Environment