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The Journal of Organic Chemistry
4-(4-Methoxyphenyl)-2H-pyran-2,6(3H)-dione (2e). white solid, 20.7 mg, 95% yield, Rf = 0.25
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(EtOAc/acetic acid 30:1). H NMR (400 MHz, CDCl3) δ 7.53 (d, J = 8.9 Hz, 2H), 7.00 (d, J = 8.9 Hz,
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2H), 6.53 (s, 1H), 3.89–3.88 (m, 5H). C{1H} NMR (126 MHz, CDCl3) δ 165.0, 162.8, 160.5, 151.9,
127.9, 125.8, 114.8, 109.4, 55.6, 33.2. IR (neat cm-1) ν 2924, 2852, 1791, 1732, 16256, 1515, 1185, 868,
619. HRMS (ESI-TOF) m/z: [M+H]+ Calcd for C12H11O4 219.0657; Found 219.0652.
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4-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2H-pyran-2,6(3H)-dione (2f). white solid, 23.2 mg, 94%
yield, Rf = 0.25 (EtOAc/acetic acid 30:1). 1H NMR (400 MHz, DMSO-d6) δ 7.36–7.32 (m, 2H), 6.95 (d,
J = 8.5 Hz, 1H), 6.70 (s, 1H), 4.29 (d, J = 6.1 Hz, 4H), 4.10 (s, 2H). 13C{1H} NMR (126 MHz, DMSO-
d6) δ 166.2, 161.4, 153.5, 146.4, 143.5, 64.4, 63.9, 33.3. IR (neat cm-1) ν 2924, 2853, 1786, 1732, 1626,
1127, 975, 887, 609. HRMS (ESI-TOF) m/z: [M+H]+ Calcd for C13H11O5 247.0606; Found 247.0604.
4-(Naphthalen-2-yl)-2H-pyran-2,6(3H)-dione (2g). white solid, 18.6 mg, 78% yield, Rf = 0.35
(EtOAc/acetic acid 30:1). 1H NMR (400 MHz, DMSO-d6) δ 8.42 (s, 1H), 8.04–7.97 (m, 4H), 7.62 (s, 2H),
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6.98 (s, 1H), 4.30 (s, 2H). C{1H} NMR (101 MHz, DMSO-d6) δ 166.2, 161.4, 153.7, 134.0, 132.5,
131.2, 129.0, 128.5, 128.0, 127.7, 127.5, 126.9, 123.2, 111.0, 33.4. IR (neat cm-1) ν 2973, 2929, 1784,
1723, 1622, 1384, 1122, 975, 814, 618. HRMS (ESI-TOF) m/z: [M+H]+ Calcd for C15H11O3 239.0708;
Found 239.0701.
4-(Naphthalen-1-yl)-2H-pyran-2,6(3H)-dione (2h). white solid, 16.4 mg, 69% yield, Rf = 0.25
(EtOAc/acetic acid 30:1). 1H NMR (400 MHz, CDCl3) δ 7.97–793 (m, 2H), 7.88–7.85 (m, 1H), 7.60–7.57
(m, 2H), 7.56–7.52 (m, 1H), 7.39–7.37 (m, 1H), 6.45 (t, J = 1.7 Hz, 1H), 3.94 (d, J = 1.7 Hz, 2H). 13C{1H}
NMR (101 MHz, CDCl3) δ 164.6, 159.8, 155.0, 133.8, 133.6, 130.7, 129.4, 129.0, 127.6, 126.8, 125.1,
124.8, 123.9, 117.8, 36.8. IR (neat cm-1) ν 2964, 2926, 2876, 1794, 1739, 1684, 1519, 1207, 776, 700.
HRMS (ESI-TOF) m/z: [M-H]- Calcd for C15H9O3 237.0552; Found 237.0553.
4-([1,1'-Biphenyl]-4-yl)-2H-pyran-2,6(3H)-dione (2i). white solid, 20.6 mg, 78% yield, Rf = 0.30
(EtOAc/acetic acid 30:1). 1H NMR (400 MHz, DMSO-d6) δ 7.91 (d, J = 8.1 Hz, 2H), 7.82–7.75 (m, 4H),
7.50 (t, J = 7.5 Hz, 2H), 7.42 (t, J = 7.2 Hz, 1H), 6.87 (s, 1H), 4.21 (s, 2H). 13C{1H} NMR (101 MHz,
DMSO-d6) δ 166.2, 161.4, 153.6, 142.9, 138.8, 132.9, 129.1, 128.2, 127.5, 127.0, 126.8, 110.5, 33.4. IR
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