The Journal of Organic Chemistry
Page 16 of 29
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Yield 244 mg, 58%. Yellow oil. H NMR (400 MHz, CDCl3) δ 7.71-7.67 (m, 4H), 7.63 (d, J = 7.9 Hz, 1H),
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7.53-7.46 (m, 2H), 7.37-7.25 (m, 7H), 7.19 (m, 5H), 7.03 (d, J = 16.4 Hz, 1H), 3.01 (s, 1H). C{1H} NMR
(100 MHz, CDCl3) δ 145.1, 139.1, 135.6, 133.5, 133.0, 129.2, 129.1, 128.9, 128.5, 128.0, 127.9, 127.5, 127.0,
126.2, 124.7, 121.4, 97.0, 85.8, 75.1. HRMS (ESI-TOF) (m/z): [M+H]+ calcd. for C29H22ClO, 421.1359, found:
421.1359.
(E)-3-(2-Styrylphenyl)-1,1-di-p-tolylprop-2-yn-1-ol (1j).
Yield 219 mg, 53%. Yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.62-7.59 (m, 1H), 7.57-7.55 (m, 4H), 7.46 (d,
J = 7.5 Hz, 1H), 7.32 (d, J = 6.8 Hz, 2H), 7.26-7.19 (m, 4H), 7.14-7.04 (m, 6H), 3.00 (d, J = 1.9 Hz, 1H), 2.26
(d, J = 6.2 Hz, 6H). 13C{1H} NMR (100 MHz, CDCl3) δ 141.3, 138.2, 136.1, 136.0, 131.7, 129.3, 127.9, 127.7,
127.5, 126.7, 126.0, 125.7, 125.4, 124.9, 123.4, 120.4, 96.1, 84.3, 73.7, 20.0. HRMS (ESI-TOF) (m/z): [M+H]+
calcd. for C31H27O, 415.2062, found: 415.2076.
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(E)-1,1-Bis(4-methoxyphenyl)-3-(2-styrylphenyl)prop-2-yn-1-ol (1k).
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Yield 316 mg, 71%. Yellow oil. H NMR (400 MHz, CDCl3) δ 7.63 (d, J = 7.8 Hz, 1H), 7.59-7.55 (m, 5H),
7.45-7.43 (m, 1H), 7.34-7.17 (m, 6H), 7.17-7.04 (m, 2H), 6.84-6.76 (m, 4H), 3.69 (s, 6H), 3.31 (s, 1H). 13C{1H}
NMR (100 MHz, CDCl3) δ 159.1, 139.4, 137.8, 17.2, 132.9, 130.5,129.0, 128.8, 128.0, 127.6, 127.3, 127.0,
126.6, 124.7, 121.6, 113.8, 97.5, 85.4, 74.5, 55.3. HRMS (ESI-TOF) (m/z): [M+H]+ calcd. for C31H27O3,
447,1960, found: 447.1944.
(E)-1,1-Bis(4-fluorophenyl)-3-(2-styrylphenyl)prop-2-yn-1-ol (1l).
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Yield 180 mg, 44%. Yellow oil. H NMR (400 MHz, CDCl3) δ 7.59 (d, J = 7.9 Hz, 1H), 7.57-7.51 (m, 4H),
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7.42-7.37 (m, 2H), 7.28-7.08 (m, 7H), 7.02 (d, J = 16.3 Hz, 1H), 6.95-6.87 (m, 4H), 2.99 (s, 1H). C{1H}
NMR (100 MHz, CDCl3) δ 162.3 (d, J = 245 Hz), 140.9, 139.5, 137.0, 132.8, 130.8, 129.3, 128.8, 128.1,
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127.3, 126.8, 126.2, 124.7, 120.9, 115.3 (d, J = 22 Hz), 96.2, 86.3, 74.2, 29.8. HRMS (ESI-TOF) (m/z):
[M+H]+ calcd. for C29H21F2O, 423.1560, found: 423.1561.
(E)-3-(2-(4-Chlorostyryl)phenyl)-1,1-di-p-tolylprop-2-yn-1-ol (1m).
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Yield 273 mg, 61%. Yellow oil. H NMR (400 MHz, CDCl3) δ 7.66 (d, J = 7.9 Hz, 1H), 7.60-7.49 (m, 6H),
7.33 (t, J = 7.6 Hz, 1H), 7.26-7.19 (m, 5H), 7.14-7.12 (m, 4H), 7.06 (d, J = 16.4 Hz, 1H), 3.00-2.65 (m, 1H),
2.34 (s, 6H). 13C{1H} NMR (100 MHz, CDCl3) δ 142.3, 139.1, 137.5, 135.7, 133.4, 132.9, 129.1, 129.0, 129.0,
128.8, 128.0, 127.4, 127.2, 126.0, 124.7, 121.6, 97.3, 85.3, 74.9, 21.1. HRMS (ESI-TOF) (m/z): [M+H]+ calcd.
for C31H26ClO, 449.1672, found: 449.1662.
(E)-1,1-Bis(4-methoxyphenyl)-3-(2-(4-methylstyryl)phenyl)prop-2-yn-1-ol (1n).
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Yield 248 mg, 54%. Yellow oil. H NMR (400 MHz, CDCl3) δ 7.55 (d, J = 7.9 Hz, 1H), 7.51-7.45 (m, 4H),
7.45-7.35 (m, 2H), 7.18 (s, 1H), 7.13 (d, J = 8.0 Hz, 2H), 7.05 (s, 1H), 7.01-6.93 (m, 3H), 6.76-6.68 (m, 5H),
3.64 (s, 6H), 3.01 (s, 1H), 2.23 (s, 3H). 13C{1H} NMR (100 MHz, CDCl3) δ 159.1, 139.6, 137.8, 137.7, 134.4,
132.8, 130.5, 129.5, 128.9, 127.5, 127.0, 126.8, 125.6, 124.6, 121.4, 113.7, 97.3, 85.5, 74.4, 55.3, 21.4. HRMS
(ESI-TOF) (m/z): [M+H]+ calcd. for C32H29O3, 461.2117, found: 461.2115.
(E)-1,1-Bis(4-fluorophenyl)-3-(2-(4-methylstyryl)phenyl)prop-2-yn-1-ol (1o).
Yield 208 mg, 56%. Yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.70-7.61 (m, 5H), 7.49-7.45 (m, 2H), 7.41 (d,
J = 7.2 Hz, 1H), 7.34-7.30 (m, 3H), 7.21-6.97 (m, 7H), 3.02 (br, 1H), 2.35 (s, 3H). 13C{1H} NMR (100 MHz,
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CDCl3) δ 162.3 (d, J = 244 Hz), 142.2, 141.5, 139.4, 137.0, 134.8, 132.8, 130.7, 129.4, 128.0, 127.9, 127.0,
126.7, 124.6, 122.2 (d, 2J = 22 Hz), 115.3 (d, 2J = 21 Hz), 96.1, 86.3, 74.2, 29.8, 21.3. HRMS (ESI-TOF) (m/z):
[M+H]+ calcd. for C30H23F2O, 437.1717, found: 437.1715.
(E)-1-Phenyl-3-(2-styrylphenyl)-1-(p-tolyl)prop-2-yn-1-ol (1p).
Yield 180 mg, 45%. Yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.71-7.68 (m, 3H), 7.61-7.57 (m, 3H), 7.52 (d,
J = 7.7 Hz, 1H), 7.38-7.23 (m, 9H), 7.23-7.17 (m, 1H), 7.15-7.09 (m, 3H), 2.95 (s, 1H), 2.33 (s, 3H). 13C{1H}
NMR (100 MHz, CDCl3) δ 145.2, 142.3, 139.4, 137.5, 137.2, 132.9, 130.5, 129.1, 129.0, 128.7, 128.4, 127.9,
127.7, 127.2, 126.9, 126.5, 126.2, 126.1, 124.6, 121.4, 97.0, 85.7, 75.0, 21.2. HRMS (ESI-TOF) (m/z): [M+H]+
calcd. for C30H25O, 401.1905, found: 401.1904.
(E)-1-(4-Chlorophenyl)-1-phenyl-3-(2-styrylphenyl)prop-2-yn-1-ol (1q).
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Yield 282 mg, 67%. Yellow oil. H NMR (400 MHz, CDCl3) δ 7.67-7.60 (m, 3H), 7.58 (d, J = 8.6 Hz, 2H),
7.51 (d, J = 16.4 Hz, 1H), 7.45 (d, J = 7.7 Hz, 1H), 7.33-7.19 (m, 10H), 7.15-7.09 (m, 1H), 7.07 (d, J = 16.4 Hz,
1H), 3.22 (s, 1H). 13C{1H} NMR (100 MHz, CDCl3) δ 144.8, 143.9, 139.6, 137.1, 133.7, 133.0, 130.8, 129.3,
128.9, 128.7, 128.2, 128.1, 127.7, 127.4, 126.9, 126.4, 126.2, 124.8, 121.2, 96.4, 86.3, 74.8, 14.3. HRMS (ESI-
TOF) (m/z): [M+H]+ calcd. for C29H22ClO, 421.1359, found: 421.1348.
(E)-Ethyl-3-(2-(3-hydroxy-3,3-diphenylprop-1-yn-1-yl)-5-methoxyphenyl)acrylate (1r).
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Yield 324 mg, 79%. Yellow oil. H NMR (400 MHz, CDCl3) δ 8.15 (d, J = 16.1 Hz, 1H), 7.69-7.67 (m, 4H),
7.42-7.40 (m,1H),7.37-7.29 (m, 4H), 7.28-7.21 (m, 2H), 7.05 (d, J = 2.4 Hz, 1H), 6.85-6.82 (m, 1H), 6.44 (d, J
= 16.0 Hz, 1H), 4.20 (q, J = 7.1 Hz, 2H), 3.81-3.79 (m, 3H), 1.24 (t, J = 7.1 Hz, 3H). 13C{1H} NMR (100 MHz,
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