The Journal of Organic Chemistry
Page 18 of 27
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7.0 Hz, 1H), 5.20 (d, J = 6.2 Hz, 1H), 3.43 (dd, J = 6.2, 2.9 Hz, 1H), 3.32 (s, 3H), 2.30 (d, J = 7.9
Hz, 1H), 1.94 (dd, J = 7.9, 2.9 Hz, 1H), 1.68 (s, 3H). 13C NMR (150 MHz, CDCl3) δ 165.1, 128.0,
126.2, 122.9, 121.1, 119.5, 118.2, 70.4, 56.2, 46.2, 39.4, 18.5, 14.4, 11.5. HRMS (ESI): calcd for
C14H15O3, [M+H] +, 231.1016; found, 231.1018.
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Compound b5’’. Colorless oil. 32 mg. Yield 27%. H NMR (400 MHz, CDCl3) δ 7.42 – 7.23 (m,
2H), 7.23 – 6.98 (m, 2H), 5.25 (s, 1H), 3.78 (s, 3H), 2.29 (s, 1H), 2.27 (d, J = 8.1 Hz, 1H), 1.99 (d, J =
8.0 Hz, 1H), 1.74 (s, 3H). 13C NMR (150 MHz, CDCl3) δ 167.4, 129.0, 127.3, 122.9, 121.2, 119.6,
117.1, 72.8, 55.1, 46.9, 40.7, 19.3, 14.9, 11.2. HRMS (ESI): calcd for C14H15O3, [M+H]+, 231.1016;
found, 231.1014.
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Compound b6’. White solid. 61 mg. Yield 50%
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Mp. 109ꢀ110 C. 1H NMR (400 MHz, CDCl3) δ
7.32 (d, J = 7.4 Hz, 1H), 7.29 – 7.21 (m, 1H), 7.14 (td, J = 7.3, 1.2 Hz, 1H), 7.10 (d, J = 7.3 Hz, 1H),
5.20 (d, J = 6.3 Hz, 1H), 3.96 – 3.57 (m, 2H), 3.41 (dd, J = 6.2, 2.9 Hz, 1H), 2.31 (d, J = 7.9 Hz, 1H),
1.94 (dd, J = 7.9, 2.9 Hz, 1H), 1.68 (s, 3H), 0.89 (t, J = 7.1 Hz, 3H). 13C NMR (150 MHz, CDCl3) δ
170.0, 133.5, 131.4, 128.2, 126.3, 124.6, 123.7, 75.8, 61.5, 60.3, 44.8, 23.8, 19.8, 16.8, 13.8. HRMS
(ESI): calcd for C15H17O3, [M+H] +, 245.1172; found, 245.1173.
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Compound b6’’. Colorless oil. 27 mg. Yield 23%. H NMR (400 MHz, CDCl3) δ 7.44 – 7.23 (m,
2H), 7.23 – 6.94 (m, 2H), 5.24 (s, 1H), 4.23 (qd, J = 7.1, 1.1 Hz, 2H), 2.36 – 2.12 (m, 2H), 1.99 (d, J =
8.0 Hz, 1H), 1.74 (s, 3H), 1.32 (t, J = 7.1 Hz, 3H). 13C NMR (150 MHz, CDCl3) δ 172.3, 134.3, 132.7,
128.1, 126.5, 124.9, 122.4, 78.2, 61.1, 60.4, 46.2, 24.7, 20.3, 16.5, 14.2. HRMS (ESI): calcd for
C15H17O3, [M+H] +, 245.1172; found, 245.1174.
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Compound b7’. White solid. 66 mg. Yield 49%. H NMR (400 MHz, CDCl3) δ 7.31 (d, J = 7.2 Hz,
1H), 7.29 – 7.23 (m, 1H), 7.14 (td, J = 7.3, 1.2 Hz, 1H), 7.09 (d, J = 6.6 Hz, 1H), 5.20 (d, J = 6.2 Hz,
1H), 3.72 (qt, J = 10.8, 6.5 Hz, 2H), 3.42 (dd, J = 6.2, 2.9 Hz, 1H), 2.30 (d, J = 7.9 Hz, 1H), 1.94 (dd, J
= 7.9, 2.9 Hz, 1H), 1.68 (s, 3H), 1.38 – 1.20 (m, 2H), 1.20 – 1.07 (m, 2H), 0.82 (t, J = 7.3 Hz, 3H).13C
NMR (150 MHz, CDCl3) δ 170.1, 133.4, 131.4, 128.1, 126.4, 124.7, 123.7, 75.7, 64.2, 61.4, 44.8, 30.4,
23.8, 19.8, 18.9, 16.8, 13.6. HRMS (ESI): calcd for C17H21O3, [M+H] +, 273.1485; found, 273.1489.
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Compound b7’’. Colorless oil. 31 mg. Yield 23%. H NMR (400 MHz, CDCl3) δ 7.35 – 7.19 (m,
2H), 7.22 – 6.81 (m, 2H), 5.23 (s, 1H), 4.47 – 3.77 (m, 2H), 2.27 (d, J = 8.0 Hz, 2H), 1.99 (d, J = 8.0
Hz, 1H), 1.73 (s, 3H), 1.70 – 1.59 (m, 2H), 1.54 – 1.31 (m, 2H), 0.96 (t, J = 7.4 Hz, 3H). 13C NMR
(150 MHz, CDCl3) δ 172.3, 134.4, 132.7, 128.1, 126.5, 124.9, 122.4, 78.2, 64.9, 60.3, 46.2, 30.6, 24.7,
20.3, 19.1, 16.5, 13.7. HRMS (ESI): calcd for C17H21O3, [M+H] +, 273.1485; found, 273.1486.
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Compound b8’. White solid. 64 mg. Yield 48%
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Mp. 105ꢀ106 C. 1H NMR (400 MHz, CDCl3) δ
7.32 (d, J = 7.4 Hz, 1H), 7.28 – 7.21 (m, 1H), 7.15 (td, J = 7.2, 1.2 Hz, 1H), 7.12 (d, J = 7.3 Hz, 1H),
5.13 (d, J = 6.3 Hz, 1H), 3.35 (dd, J = 6.3, 2.9 Hz, 1H), 2.27 (d, J = 7.9 Hz, 1H), 1.90 (dd, J = 7.9, 2.9
Hz, 1H), 1.67 (s, 3H), 1.08 (s, 9H). 13C NMR (150 MHz, CDCl3) δ 169.3, 133.7, 131.6, 128.1, 126.4,
124.5, 124.1, 80.7, 75.9, 61.5, 45.7, 27.5, 23.8, 20.0, 16.8. HRMS (ESI): calcd for C17H21O3, [M+H]+,
273.1485; found, 273.1483.
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Compound b8’’. Colorless oil. 28 mg. Yield 21%. H NMR (400 MHz, CDCl3) δ 7.37 – 7.24 (m,
2H), 7.16 (dd, J = 4.5, 2.1 Hz, 2H), 5.19 (s, 1H), 2.24 (d, J = 8.0 Hz, 1H), 2.17 (s, 1H), 1.93 (d, J = 8.0
Hz, 1H), 1.73 (s, 3H), 1.51 (s, 9H). 13C NMR (150 MHz, CDCl3) δ 171.5, 134.6, 132.8, 128.0, 126.4,
124.8, 122.4, 81.2, 78.4, 60.3, 47.1, 28.1, 24.7, 20.5, 16.6. HRMS (ESI): calcd for C17H21O3, [M+H]+,
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