The Journal of Organic Chemistry
Page 14 of 18
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liquid 5aꢀH (16.8 mg, 0.0499 mmol, 10%).
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(E)ꢀ2,6ꢀDiꢀtertꢀbutylꢀ4ꢀ(2ꢀ(4ꢀmethoxyphenyl)ꢀ1ꢀ(phenylsulfonyl)vinyl)phenol (4aꢀH): white solid, mp 147−152 °C. 1H NMR (599 MHz,
CDCl3) δ 7.84 (s, 1 H, Hꢀ1), 7.66 – 7.57 (m, 2 H, Hꢀ15 x 2), 7.50 (t, J = 7.4 Hz, 1 H, Hꢀ17), 7.37 (dd, J = 8.5, 7.1 Hz, 2 H, Hꢀ16 x 2), 7.05 (d, J =
8.9 Hz, 2 H, Hꢀ3 x 2), 6.71 (s, 2 H, Hꢀ9 x 2), 6.69 (d, J = 9.0 Hz, 2 H, Hꢀ4 x 2), 5.31 (s, 1 H, OH), 3.75 (s, 3 H, Hꢀ6 x 3), 1.28 (s, 18 H, Hꢀ13 x 18).
13C NMR (151 MHz, CDCl3) δ 161.03 (Cꢀ5), 154.60 (Cꢀ11), 139.54 (Cꢀ14), 139.47 (Cꢀ7), 136.62 (Cꢀ1), 136.55 (Cꢀ10 x 2), 132.83 (Cꢀ17),
132.35 (Cꢀ3 X 2), 128.83 (Cꢀ15 x 2), 128.58 (Cꢀ16 x 2), 127.71 (Cꢀ9 x 2), 125.96 (Cꢀ2), 122.10 (Cꢀ8), 113.96 (Cꢀ4 x 2), 55.41 (Cꢀ6), 34.39
(Cꢀ12 x 2), 30.33 (Cꢀ13 x 6). HRMS (EI) m/z: [M+] calcd for C29H34O4S 478.2172, found 478.2172. IR (ATR) v (cmꢀ1) = 3552, 2949, 1606, 1513,
1444, 1419, 1376, 1305, 1282, 1256, 1236, 1177, 1147, 1110, 1036, 1023, 981, 895, 840, 804, 765, 751, 714, 689, 666.
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2,6ꢀDiꢀtertꢀbutylꢀ4ꢀ((4ꢀmethoxyphenyl)ethynyl)phenol (5aꢀH): colorless liquid. 1H NMR (599 MHz, CDCl3) δ 7.46 (d, J = 8.7 Hz, 2 H,
Hꢀ4 x 2), 7.34 (s, 2 H, Hꢀ9 x 2), 6.86 (d, J = 8.7 Hz, 2 H, Hꢀ3 x 2), 5.35 (s, 1 H, OH), 3.82 (s, 3 H, Hꢀ1 x 3), 1.45 (s, 18 H, Hꢀ12 x 18). 13C NMR
(151 MHz, CDCl3) δ 159.4 (Cꢀ2), 154.3 (Cꢀ13), 136.2 (Cꢀ10 x 2), 133.0 (Cꢀ4 x 2), 128.6 (Cꢀ9 x 2), 116.1 (Cꢀ5), 114.5 (Cꢀ8), 114.1 (Cꢀ3 x 2),
89.3 (Cꢀ7), 87.0 (Cꢀ6), 55.4 (Cꢀ1), 34.5 (Cꢀ11 x 2), 30.4 (Cꢀ12 x 6). HRMS (EI) m/z: [M+] calcd for C23H28O2 336.2084, found 336.2081. IR
(ATR) v (cmꢀ1) = 3625, 2956, 1606, 1509, 1433, 1287, 1174,1152,1119, 1105, 1031, 885, 830, 806, 774, 757.
(E)ꢀ2,6ꢀDiꢀtertꢀbutylꢀ4ꢀ(1ꢀ((4ꢀchlorophenyl)sulfonyl)ꢀ2ꢀ(4ꢀmethoxyphenyl)vinyl)phenol (4bꢀH). General procedure 3 was applied to
1bꢀH (225 mg, 1.00 mmol), 2c (162 mg, 0.500 mmol) and tꢀBuOK (112 mg, 1.00 mmol). 4bꢀH was obtained as a pale yellow liquid (156 mg,
0.305 mmol, 61%) 1H NMR (400 MHz, CDCl3) δ 7.82 (s, 1 H, Hꢀ1), 7.52 (d, J = 8.6 Hz, 2 H, Hꢀ15 x 2), 7.34 (d, J = 8.5 Hz, 2 H, Hꢀ16 x 2), 7.06
(d, J = 8.8 Hz, 2 H, Hꢀ3 x 2), 6.72 (s, 2 H, Hꢀ9 x 2), 6.70 (d, J = 8.8 Hz, 2 H, Hꢀ4 x 2), 5.34 (s, 1 H, OH), 3.76 (s, 3 H, Hꢀ6 x 3), 1.30 (s, 18 H,
Hꢀ13 x 18). 13C NMR (101 MHz, CDCl3) δ 161.19 (Cꢀ5), 154.72 (Cꢀ11), 139.52 (Cꢀ17), 139.21 (Cꢀ7), 138.03 (Cꢀ14), 136.82 (Cꢀ1), 136.76 (Cꢀ10
x 2), 132.42 (Cꢀ3 x 2), 130.29 (Cꢀ15 x 2), 128.80 (Cꢀ16 x 2), 127.76 (Cꢀ9 x 2), 125.78 (Cꢀ2), 121.88 (Cꢀ8), 114.02 (Cꢀ4 x 2), 55.43 (Cꢀ6), 34.42
(Cꢀ12 x 2), 30.33 (Cꢀ13 x 6). HRMS (EI) m/z: [M+] calcd for C29H33ClO4S 512.1783, found 512.1792. IR (ATR) v (cmꢀ1) = 3628, 2955, 1601,
1510, 1474, 1436, 1375, 1303, 1253, 1176, 1145, 1029, 982, 828, 765, 706, 669.
(E)ꢀ2,6ꢀDiꢀtertꢀbutylꢀ4ꢀ(1ꢀ((4ꢀcyanophenyl)sulfonyl)ꢀ2ꢀ(4ꢀmethoxyphenyl)vinyl)phenol (4cꢀH): General procedure 3 was applied to
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