The Journal of Organic Chemistry
Page 14 of 22
7.06 (d, J = 7.5 Hz, 1H), 6.96 (s, 1H), 2.58 (s, 3H), 2.41 (s, 3H); C{1H} NMR (CDCl3, 125 MHz) δ
155.7, 153.9, 138.3, 130.6, 129.2, 128.7, 128.6, 125.4, 125.1, 122.9, 122.1, 121.3, 118.3, 101.4, 21.5,
15.0; MS (ESI): 223 [M+H]+; HRMS (ESI) calcd for C16H15O [M+H]+: 223.1117; found: 223.1116; IR
(neat) ν 3057, 2917, 2852, 1612, 1574, 1484, 1451, 1414, 1349, 1291, 1214, 1186, 1091, 1040, 928, 864
cmꢀ1.
13
1
2
3
4
5
6
7
8
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
Compound 4v: colorless liquid (79.9 mg, 72%); 1H NMR (CDCl3, 500 MHz, TMS) δ 7.83 (d, J = 7.0
Hz, 1H), 7.41 (d, J = 8.0 Hz, 1H), 7.29ꢀ7.23 (m, 3H), 7.12 (t, J = 7.5 Hz, 1H), 7.07 (d, J = 7.0 Hz, 1H),
6.85 (s, 1H), 2.564 (s, 3H), 2.559 (s, 3H); 13C{1H} NMR (CDCl3, 125 MHz) δ 155.4, 153.5, 135.8,
131.3, 130.1, 128.6, 128.4, 128.1, 126.0, 125.1, 122.8, 121.3, 118.3, 105.2, 21.9, 15.0; MS (ESI): 223
[M+H]+; HRMS (ESI) calcd for C16H15O [M+H]+: 223.1117; found: 223.1121; IR (neat) ν 3067, 2915,
2855, 1484, 1457, 1418, 1381, 1295, 1209, 1179, 1020, 911, 856, 806, 768, 743, 717 cmꢀ1.
Compound 4w: white solid (79.6 mg, 68%); mp: 88ꢀ89 °C; 1H NMR (CDCl3, 500 MHz, TMS) δ 7.78
(d, J = 8.5 Hz, 2H), 7.43 (d, J = 8.5 Hz, 2H), 7.36 (d, J = 7.5 Hz, 1H), 7.10 (t, J = 7.5 Hz, 1H), 7.05 (d, J
= 7.0 Hz, 1H), 6.94 (s, 1H), 6.71 (dd, J = 17.5, 11.0 Hz, 1H), 5.77 (d, J = 17.5 Hz, 1H), 5.26 (d, J = 11.0
Hz, 1H), 2.56 (s, 3H); 13C{1H} NMR (CDCl3, 125 MHz) δ 155.3, 153.9, 137.6, 136.3, 130.0, 128.7,
126.6, 125.2, 125.0, 123.0, 121.4, 118.3, 114.3, 101.7, 15.0; MS (ESI): 235 [M+H]+; HRMS (ESI) calcd
for C17H15O [M+H]+: 235.1117; found: 235.1127; IR (neat) ν 2920, 2847, 1697, 1621, 1607, 1582,
1500, 1486, 1407, 1351, 1295, 1264, 1205, 1180, 1031, 1008, 990, 913, 845, 812, 771, 743 cmꢀ1.
1
Compound 4x: white solid (80.6 mg, 76%); mp: 130ꢀ131 °C; H NMR (CDCl3, 500 MHz, TMS) δ
7.81 (d, J = 7.0 Hz, 2H), 7.43ꢀ7.38 (m, 3H), 7.34 (t, J = 7.5 Hz, 1H), 7.19 (dd, J = 8.5, 2.5 Hz, 1H), 6.97
13
(td, J = 9.0, 2.5 Hz, 1H), 6.92 (s, 1H); C{1H} NMR (CDCl3, 125 MHz) δ 159.3 (d, JCꢀF = 236.5 Hz),
157.7, 151.1, 130.1 (d, JCꢀF = 8.25 Hz), 129.9, 128.8 (d, J = 7.375 Hz), 125.0, 111.8 (d, JCꢀF = 24.375
Hz); 111.7 (d, JCꢀF = 7.625 Hz); 106.3 (d, JCꢀF = 25.0 Hz), 101.4 (d, J = 4.0 Hz); MS (ESI): 213 [M+H]+;
HRMS (ESI) calcd for C14H10FO [M+H]+: 213.0710; found: 213.0699; IR (neat) ν 3100, 3065, 3040,
2914, 2847, 1593, 1457, 1441, 1341, 1272, 1189, 1129, 1020, 950, 915, 866, 799, 762, 741 cmꢀ1.
14
ACS Paragon Plus Environment