The Journal of Organic Chemistry
Page 14 of 21
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(5,6-Dimethoxybenzofuran-2-yl)(phenyl)methanone (3p): Yellow solid (74 mg, 69% yield); Rf = 0.4
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(hexanes:EtOAc = 17:3); mp = 127–129 °C; H NMR (300 MHz, CDCl3) δ 8.00 (d, J = 7.2 Hz, 2H),
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7.61 (t, J = 7.3 Hz, 1H), 7.51 (t, J = 7.3 Hz, 2H), 7.45 (s, 1H), 7.10 (s, 1H), 7.06 (s, 1H), 3.96 (s, 3H),
3.93 (s, 3H); 13C NMR (126 MHz, CDCl3) δ 183.6, 152.0, 147.9, 137.6, 132.6, 129.3, 128.5, 119.2,
117.4, 102.8, 95.2, 56.4; cmꢀ1; IR (neat): υmax 300+, 2934, 1642, 1541, 1467, 1298, 1119, 969, 700 cmꢀ1;
HRMS (ESIꢀTOF) m/z: [M+H]+ Calcd for C17H15O4 283.0970; found : 283.0983.
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[1,3]Dioxolo[4,5-f]benzofuran-6-yl(phenyl)methanone (3q): Pale yellow solid (81 mg, 79% yield); Rf
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= 0.5 (hexanes:EtOAc = 17:3); mp = 152–154 °C; H NMR (400 MHz, CDCl3) δ 8.0 ꢀ 7.97 (m, 2H),
7.64 – 7.57 (m, 1H), 7.55 – 7.48 (m, 2H), 7.40 (s, 1H), 7.06 (s, 1H), 6.99 (d, J = 1.3 Hz, 1H), 6.04 (d, J
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= 1.3 Hz, 2H); C NMR (75 MHz, CDCl3) δ 183.5, 152.5, 152.3, 150.0, 145.9, 137.5, 132.6, 129.3,
128.5, 120.6, 117.6, 102.0, 100.2, 93.9; IR (neat): υmax 2905, 1618, 1458, 1236, 972, 795, 697 cmꢀ1;
HRMS (ESIꢀTOF) m/z: [M+H]+ Calcd for C16H11O4 267.0657; found: 267.0668.
[1,3]Dioxolo[4,5-f]benzofuran-6-yl(4-methoxyphenyl)methanone (3r) : Pale yellow solid (82 mg,
81% yield); Rf = 0.5 (hexanes:EtOAc = 8.5:1.5); mp = 164–166 °C; 1H NMR (400 MHz, CDCl3) δ 8.11
– 8.02 (m, 2H), 7.42 (d, J = 0.7 Hz, 1H), 7.07 (s, 1H), 7.04 – 6.98 (m, 3H), 6.05 (s, 2H), 3.91 (s, 3H; 13C
NMR (101 MHz, CDCl3) δ 182.0, 163.4, 152.8, 152.2, 149.7, 145.8, 131.7, 130.1, 120.7, 116.6, 113.8,
101.9, 100.2, 93.9, 55.5; IR (neat): υmax 2936, 2905, 1618, 1458, 1236, 1171, 972, 795, 697 cmꢀ1; HRMS
(ESIꢀTOF) m/z: [M+Na]+ Calcd for C17H12O5Na 319.0582; found: 319.0580.
(5,6-Difluorobenzofuran-2-yl)(phenyl)methanone (3s): White solid (68 mg, 69% yield); Rf = 0.4
(hexanes:EtOAc = 19:1); mp = 117–119 °C; 1H NMR (400 MHz, CDCl3) δ 8.08ꢀ8.01 (m, 2H), 7.70 –
7.64 (m, 1H), 7.62 (d, J = 0.6 Hz, 1H), 7.71ꢀ7.64 (m, 2H), 7.42 – 7.30 (m, 2H); 13C NMR (101 MHz,
CDCl3) δ 183.80, 170.41, 153.40, 152.3 (d, JCF = 6.4 Hz),, 136.63, 133.39, 129.50, 128.74, 117.8 (d,
JCF = 22.1 Hz),, 112.3 (d, JCF = 4.1 Hz),, 108.5 (d, JCF = 5.4 Hz),, 108.4 (d, JCF = 5.3 Hz). IR (neat): υmax
2925, 2825, 1658, 1549, 1332, 1122, 722 cmꢀ1; HRMS (ESIꢀTOF) m/z: [M+H]+ Calcd for C15H9F2O2
259.0571; found: 259.0577.
Naphtho[2,3-b]furan-2-yl(phenyl)methanone (3t): Pale yellow solid (77 mg, 74% yield); Rf = 0.5
(hexanes:EtOAc = 19:1); mp = 99–101 °C; 1H NMR (400 MHz, CDCl3) δ 8.25 (s, 1H), 8.12 – 8.07 (m,
2H), 8.05 (s, 1H), 8.01 – 7.95 (m, 2H), 7.70 – 7.62 (m, 2H), 7.60 – 7.43 (m, 4H);13C NMR (101 MHz,
CDCl3) δ 184.7, 154.1, 154.0, 137.2, 133.6, 133.1, 130.8, 129.6, 128.6, 128.5, 128.1, 127.7, 126.3, 124.7,
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