The Journal of Organic Chemistry
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100.4, 31.4, 24.5, 22.1, 21.4, 13.8; HRMS (ESI) calcd for C20H21-
ClNaO3 (M + Na)+ 367.1077, found 367.1077.
Compound 3ad. 75 mg, 77% yield, colorless oil; H NMR (600
Hz, 3H); 13C NMR (151 MHz, CDCl3): δ 164.2, 161.4, 155.5, 148.4,
139.7, 132.7, 129.2, 124.4, 120.1, 118.5, 115.6, 114.6, 100.6, 31.4, 24.4,
22.1, 21.3, 13.8; HRMS (ESI) calcd for C20H22NaO4 (M + Na)+
349.1416, found 349.1414.
1
MHz, CDCl3): δ 7.93 (d, J = 8.5 Hz, 2H), 7.58 (d, J = 8.5 Hz, 2H),
7.21−7.17 (m, 1H), 7.00−6.97 (m, 2H), 6.89 (d, J = 7.5 Hz, 1H), 4.81
(t, J = 7.6 Hz, 1H), 2.33 (s, 3H), 2.04−1,98 (m, 2H), 1.39−1.30 (m,
4H), 0.87 (t, J = 7.2 Hz, 3H); 13C NMR (151 MHz, CDCl3): δ 162.9,
155.4, 148.4, 139.7, 131.9, 131.6, 129.2, 129.0, 127.4, 124.4, 118.5,
114.7, 100.4, 31.4, 24.5, 22.1, 21.3, 13.8; HRMS (ESI) calcd for
C20H21BrNaO3 (M + Na)+ 411.0572, found 411.0567.
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Compound 3am. 62 mg, 76% yield, colorless oil; H NMR (600
MHz, CDCl3): δ 10.42 (s, 1H), 7.93 (dd, J = 8.0, 1.5 Hz, 1H), 7.56−
7.51 (m, 1H), 7.28−7.23 (m, 1H), 7.07−7.02 (m, 3H), 6.96−6.93 (m,
2H), 4.89 (t, J = 7.6 Hz, 1H), 2.39 (s, 3H), 2.10−2.06 (m, 2H), 1.45−
1.37 (m, 4H), 0.93 (t, J = 7.2 Hz, 3H); 13C NMR (151 MHz, CDCl3):
δ 167.5, 162.2, 155.4, 147.8, 139.8, 136.6, 130.3, 129.3, 124.6, 119.4,
118.4, 117.8, 114.6, 111.0, 100.9, 31.4, 24.4, 22.1, 21.4, 13.8; HRMS
(ESI) calcd for C20H22NaO4 (M + Na)+ 349.1416, found 349.1396.
Compound 3an. 44 mg, 56% yield, yellow oil; 1H NMR (600 MHz,
CDCl3): δ 8.84 (d, J = 3.2 Hz, 2H), 7.91 (d, J = 5.1 Hz, 2H), 7.26−
7.22 (m, 1H), 7.02−6.99 (m, 2H), 6.94 (d, J = 7.5 Hz, 1H), 4.86 (t, J =
7.6 Hz, 1H), 2.37 (s, 3H), 2.06−2.01 (m, 2H), 1.43−1.33 (m, 4H),
0.91 (t, J = 7.2 Hz, 3H); 13C NMR (151 MHz, CDCl3): δ 162.2, 155.3,
150.7, 148.2, 139.9, 135.9, 129.3, 124.7, 123.2, 118.5, 114.6, 100.7,
31.4, 24.5, 22.1, 21.4, 13.8; HRMS (ESI) calcd for C19H21NNaO3 (M
+ Na)+ 334.1419, found 334.1417.
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Compound 3ae. 80 mg, 73% yield, colorless oil; H NMR (600
MHz, CDCl3): δ 7.87−7.84 (m, 2H), 7.83−7.80 (m, 2H), 7.26−7.22
(m, 1H), 7.06−7.02 (m, 2H), 6.94 (d, J = 7.5 Hz, 1H), 4.85 (t, J = 7.6
Hz, 1H), 2.38 (s, 3H), 2.08−2.02 (m, 2H), 1.44−1.36 (m, 4H), 0.92
(t, J = 7.2 Hz, 3H); 13C NMR (151 MHz, CDCl3): δ 163.1, 155.4,
148.4, 139.7, 137.9, 131.5, 129.2, 128.0, 124.4, 118.5, 114.7, 101.9,
100.4, 31.4, 24.5, 22.1, 21.3, 13.8; HRMS (ESI) calcd for C20H21INaO3
(M + Na)+ 459.0433, found 459.0426.
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Compound 3af. 53 mg, 60% yield, colorless oil; H NMR (600
MHz, CDCl3): δ 8.30 (d, J = 8.8 Hz, 2H), 8.26−8.23 (m, 2H), 7.23−
7.19 (m, 1H), 7.01−6.97 (m, 2H), 6.92 (d, J = 7.5 Hz, 1H), 4.84 (t, J =
7.6 Hz, 1H), 2.34 (s, 3H), 2.07−1.98 (m, 2H), 1.41−1.31 (m, 4H),
0.88 (t, J = 7.2 Hz, 3H); 13C NMR (151 MHz, CDCl3): δ 161.8, 155.3,
150.9, 148.2, 139.9, 133.9, 131.3, 129.3, 124.7, 123.7, 118.5, 114.6,
100.6, 31.4, 24.5, 22.1, 21.3, 13.8; HRMS (ESI) calcd for C20H21-
NNaO5 (M + Na)+ 378.1317, found 378.1309.
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Compound 3ao. 70 mg, 88% yield, colorless oil; H NMR (600
MHz, CDCl3): δ 7.92 (d, J = 3.7 Hz, 1H), 7.65 (d, J = 4.9 Hz, 1H),
7.26−7.22 (m, 1H), 7.18−7.13 (m, 1H), 7.04−7.00 (m, 2H), 6.94 (d, J
= 7.4 Hz, 1H), 4.83 (t, J = 7.6 Hz, 1H), 2.38 (s, 3H), 2.11−2.05 (m,
2H), 1.44−1.36 (m, 4H), 0.93 (t, J = 7.1 Hz, 3H); 13C NMR (151
MHz, CDCl3): δ 159.0, 155.6, 148.4, 139.8, 135.1, 133.9, 131.8, 129.3,
128.1, 124.4, 118.6, 114.8, 100.6, 31.5, 24.5, 22.2, 21.4, 13.9; HRMS
(ESI) calcd for C18H20NaO3S (M + Na)+ 339.1031, found 339.1029.
1
Compound 3ag. 73 mg, 87% yield, colorless oil; H NMR (600
MHz, CDCl3): δ 8.20 (d, J = 8.0 Hz, 2H), 7.79 (d, J = 8.0 Hz, 2H),
7.26−7.22 (m, 1H), 7.04−7.00 (m, 2H), 6.94 (d, J = 7.5 Hz, 1H), 4.86
(t, J = 7.6 Hz, 1H), 2.37 (s, 3H), 2.10−2.00 (m, 2H), 1.44−1.32 (m,
4H), 0.91 (t, J = 7.1 Hz, 3H); 13C NMR (151 MHz, CDCl3): δ 162.0,
155.3, 148.2, 139.8, 132.3, 132.3, 130.6, 129.2, 124.6, 118.4, 117.6,
117.1, 114.6, 100.5, 31.3, 24.4, 22.0, 21.3, 13.7; HRMS (ESI) calcd for
C21H21NNaO3 (M + Na)+ 358.1419, found 358.1414.
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Compound 3ap. 71 mg, 85% yield, colorless oil; H NMR (600
MHz, CDCl3): δ 7.84 (d, J = 16.0 Hz, 1H), 7.59−7.54 (m, 2H), 7.45−
7.40 (m, 3H), 7.26−7.23 (m, 1H), 7.04−7.01 (m, 2H), 6.95 (d, J = 7.6
Hz, 1H), 6.52 (d, J = 16.0 Hz, 1H), 4.83 (t, J = 7.6 Hz, 1H), 2.39 (s,
3H), 2.10−2.04 (m, 2H), 1.44−1.38 (m, 4H), 0.95 (t, J = 7.1 Hz, 3H);
13C NMR (151 MHz, CDCl3): δ 163.8, 155.7, 148.4, 147.4, 139.7,
134.0, 130.9, 129.3, 129.0, 128.4, 124.4, 118.5, 116.2, 114.8, 100.6,
31.6, 24.6, 22.3, 21.4, 13.9; HRMS (ESI) calcd for C22H24NaO3 (M +
Na)+ 359.1623, found 359.1626.
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Compound 3ah. 77 mg, 84% yield, colorless oil; H NMR (600
MHz, CDCl3): δ 8.20−8.10 (m, 4H), 7.26−7.21 (m, 1H), 7.05−7.01
(m, 2H), 6.94 (d, J = 7.5 Hz, 1H), 4.85 (t, J = 7.6 Hz, 1H), 3.98 (s,
3H), 2.37 (s, 3H), 2.10−2.00 (m, 2H), 1.45−1.30 (m, 4H), 0.91 (t, J =
7.2 Hz, 3H); 13C NMR (151 MHz, CDCl3): δ 166.0, 162.8, 155.4,
148.4, 139.7, 134.6, 132.3, 130.1, 129.6, 129.2, 124.5, 118.5, 114.7,
100.4, 52.4, 31.4, 24.5, 22.1, 21.3, 13.8; HRMS (ESI) calcd for
C22H24NaO5 (M + Na)+ 391.1521, found 391.1521.
Compound 3aq. 61 mg, 73% yield, yellow oil; 1H NMR (600 MHz,
CDCl3): δ 8.12−8.10 (m, 2H), 7.66−7.60 (m, 1H), 7.52−7.46 (m,
2H), 7.25−7.21 (m, 1H), 7.09−7.00 (m, 3H), 4.84 (t, J = 7.6 Hz, 1H),
2.37 (s, 3H), 2.08−2.04 (m, 2H), 1.43−1.36 (m, 4H), 0.91 (t, J = 7.2
Hz, 3H); 13C NMR (151 MHz, CDCl3): δ 163.6, 155.6, 148.6, 139.7,
133.8, 130.2, 129.2, 128.6, 128.5, 126.5, 124.4, 122.2, 118.6, 114.7,
100.4, 31.5, 24.5, 22.2, 21.4, 13.8; HRMS (ESI) calcd for C22H22NaO3
(M + Na)+ 357.1467, found 357.1463.
1
Compound 3ai. 66 mg, 81% yield, colorless oil; H NMR (400
MHz, CDCl3): δ 8.00 (d, J = 8.2 Hz, 2H), 7.30−7.21 (m, 3H), 7.06−
7.00 (m, 2H), 6.92 (d, J = 7.5 Hz, 1H), 4.83 (t, J = 7.6 Hz, 1H), 2.44
(s, 3H), 2.37 (s, 3H), 2.09−2.01 (m, 2H), 1.42−1.32 (m, 4H), 0.91 (t,
J = 7.1 Hz, 3H); 13C NMR (101 MHz, CDCl3): δ 163.6, 155.6, 148.6,
144.7, 139.7, 130.3, 129.2, 129.2, 125.8, 124.3, 118.6, 114.7, 100.3,
31.5, 24.5, 22.1, 21.7, 21.4, 13.8; HRMS (ESI) calcd for C21H24NaO3
(M + Na)+ 347.1623, found 347.1622.
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Compound 3ar. 52 mg, 83% yield, colorless oil; H NMR (600
MHz, CDCl3): δ 7.22 (t, J = 7.7 Hz, 1H), 6.96−6.91 (m, 3H), 4.74 (t,
J = 7.6 Hz, 1H), 2.37 (s, 3H), 2.18 (s, 3H), 2.02−1.96 (m, 2H), 1.42−
1.35 (m, 4H), 0.93 (t, J = 7.1 Hz, 3H); 13C NMR (151 MHz, CDCl3):
δ 167.8, 155.5, 148.2, 139.7, 129.2, 124.3, 118.4, 114.6, 100.3, 31.4,
24.5, 22.2, 21.4, 20.4, 13.8; HRMS (ESI) calcd for C15H20NaO3 (M +
Na)+ 271.1310, found 271.1304.
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Compound 3aj. 68 mg, 80% yield, colorless oil; H NMR (600
MHz, CDCl3): δ 8.09−8.04 (m, 2H), 7.25−7.20 (m, 1H), 7.05−7.00
(m, 2H), 6.98−6.90 (m, 3H), 4.82 (t, J = 7.6 Hz, 1H), 3.89 (s, 3H),
2.37 (s, 3H), 2.08−2.03 (m, 2H), 1.43−1.35 (m, 4H), 0.91 (t, J = 7.2
Hz, 3H); 13C NMR (151 MHz, CDCl3): δ 164.0, 163.3, 155.7, 148.6,
139.6, 132.4, 129.2, 124.3, 120.8, 118.6, 114.7, 113.8, 100.3, 55.5, 31.5,
24.5, 22.1, 21.4, 13.8; HRMS (ESI) calcd for C21H24NaO4 (M + Na)+
363.1572, found 363.1565.
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Compound 3as. 58 mg, 80% yield, colorless oil; H NMR (600
MHz, CDCl3): δ 7.21 (t, J = 7.8 Hz, 1H), 6.97−6.91 (m, 3H), 4.72 (t,
J = 7.6 Hz, 1H), 2.36 (s, 3H), 2.01−1.95 (m, 2H), 1.43−1.33 (m, 4H),
1.24 (s, 9H), 0.93 (t, J = 7.1 Hz, 3H); 13C NMR (151 MHz, CDCl3):
δ 175.3, 155.3, 148.7, 139.5, 129.1, 124.3, 118.8, 115.0, 99.3, 38.9, 31.4,
26.1, 24.3, 22.1, 21.3, 13.8; HRMS (ESI) calcd for C18H26NaO3 (M +
Na)+ 313.1780, found 313.1774.
Compound 3ak. 33 mg, 40% yield, white solid, mp: 86−89 °C; 1H
NMR (600 MHz, CDCl3): δ 7.91 (d, J = 8.5 Hz, 2H), 7.25−7.20 (m,
1H), 7.05−7.00 (m, 2H), 6.91 (d, J = 7.4 Hz, 1H), 6.65 (d, J = 8.5 Hz,
2H), 4.80 (t, J = 7.6 Hz, 1H), 4.19 (s, 2H), 2.36 (s, 3H), 2.07−2.01
(m, 2H), 1.42−1.33 (m, 4H), 0.90 (t, J = 7.0 Hz, 3H); 13C NMR (151
MHz, CDCl3): δ 163.6, 155.7, 151.6, 148.7, 139.6, 132.4, 129.1, 124.1,
118.6, 117.6, 114.7, 113.7, 100.2, 31.5, 24.5, 22.1, 21.4, 13.8; HRMS
(ESI) calcd for C20H24NO3 (M + H)+ 326.1756, found 326.1749.
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Compound 3at. 65 mg, 76% yield, colorless oil; H NMR (600
MHz, CDCl3): δ 7.25−7.19 (m, 3H), 7.02−6.98 (m, 2H), 6.95−6.85
(m, 3H), 4.74 (t, J = 7.7 Hz, 1H), 3.70 (s, 2H), 2.35 (s, 3H), 1.90−
1.86 (m, 2H), 1.35−1.28 (m, 4H), 0.90 (t, J = 7.1 Hz, 3H); 13C NMR
(151 MHz, CDCl3): δ 168.3, 162.1 (d, J = 246.0 Hz), 155.2, 148.1,
139.6, 130.8 (d, J = 8.1 Hz), 129.2, 128.7 (d, J = 3.3 Hz), 124.4, 118.5,
115.4 (d, J = 21.5 Hz), 114.7, 100.1, 39.9, 31.3, 24.3, 22.1, 21.3, 13.7;
HRMS (ESI) calcd for C21H23FNaO3 (M + Na)+ 365.1529, found
365.1531.
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Compound 3al. 65 mg, 80% yield, white solid, mp: 63−65 °C; H
NMR (600 MHz, CDCl3): δ 8.02 (d, J = 8.8 Hz, 2H), 7.26−7.20 (m,
1H), 7.04−7.00 (m, 2H), 6.98−6.92 (m, 3H), 4.86 (t, J = 7.6 Hz, 1H),
2.36 (s, 3H), 2.10−2.00 (m, 2H), 1.50−1.30 (m, 4H), 0.91 (t, J = 7.2
1
Compound 3ba. 54 mg, 90% yield, colorless oil; H NMR (600
MHz, CDCl3): δ 8.16−8.11 (m, 2H), 7.64 (t, J = 7.4 Hz, 1H), 7.51−
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dx.doi.org/10.1021/jo501615a | J. Org. Chem. 2014, 79, 9179−9185