The Journal of Organic Chemistry
Page 26 of 33
ml) were used to furnish the product 14r (28 mg, 93%) as a yellow oil. Rf = 0.4 (EtOAc-hexane 10:90);
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IR (neat): vmax/cm-1 2950, 2840, 1693, 1658, 1485, 1545, 1509, 1250, 1020; H NMR (400 MHz,
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CDCl3) δ 1.00 (d, J = 6.8 Hz, 2H), 1.21 (d, J = 6.8 Hz, 3H), 2.10 (t, J = 1.8 Hz, 3H), 2.15 - 2.17 (m,
2H), 3.60 - 3.66 (m, 1H), 3.72 - 3.97 (m, 3H), 6.08 (s, 1H), 6.23 (s, 1H), 7.11 - 7.22 (m, 2H), 7.26 - 7.31
(m, 4H), 7.31 - 7.36 (m, 1H), 7.42 - 7.51 (m, 5H), 7.52 - 7.63 (m, 2H), 7.93 - 7.97 (m, 2H), 7.99 - 8.04
(m, 2H); 13C NMR (125 MHz, CDCl3) δ 12.9, 13.0, 13.9, 14.7, 42.3, 42.8, 50.4, 50.9, 119.0, 119.0,
122.8, 124.4, 124.6, 124.9, 126.7, 128.4, 128.4, 128.6, 128.7, 130.1, 131.1, 132.7, 132.9, 133.0, 134.8,
136.5, 139.5, 140.4, 145.4, 145.9, 146.3, 146.4, 203.4, 203.6; HRMS: m/z calcd for C19H19O [(M+H)+]:
263.1436; Found: 263.1442.
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(E)-4-(4-chlorophenyl)-1-(7-methoxy-3,6-dimethyl-1H-inden-1-yl)but-3-en-2-one (14s). According to
the general procedure of cyclization reaction, compound 13s (40 mg, 0.113 mmol) and FeCl3.6H2O (3.0
mg, 0.011 mmol), in CH2Cl2 (3 ml) were used to furnish the product 14s (39 mg, 98%) as a yellow oil.
Rf = 0.3 (EtOAc-hexane 5:95); IR (neat): vmax/cm-1 2928, 1691, 1665, 1612, 1490, 1349, 1244, 1198,
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1122, 1088; H NMR (500 MHz, CDCl3) δ 2.09 (br. s., 3H), 2.33 (s, 3H), 2.52 (dd, J = 17.2, 10.9 Hz,
1H), 3.63 - 3.69 (m, 1H), 3.84 (s, 4H), 4.02 - 4.20 (m, 1H), 6.19 (br. s., 1H), 6.70 (d, J = 16.6 Hz, 1H),
6.98 (d, J = 7.4 Hz, 1H), 7.15 (d, J = 7.4 Hz, 1H), 7.36 (d, J = 8.6 Hz, 2H), 7.44 (d, J = 8.6 Hz, 2H),
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7.49 (d, J = 16.0 Hz, 1H); C NMR (125 MHz, CDCl3) δ 13.0, 15.8, 40.6, 42.9, 59.9, 114.9, 126.8,
127.7, 129.2, 129.4, 130.1, 132.9, 136.3, 137.5, 139.1, 141.2, 141.2, 145.8, 154.5, 199.3; HRMS: m/z
calcd for C22H21ClNaO2 [(M+Na)+]: 375.1128; Found: 375.1120.
(E)-1-(7-methoxy-3,6-dimethyl-1H-inden-1-yl)-4-phenylbut-3-en-2-one (14t). According to the general
procedure of cyclization reaction, compound 13t (44 mg, 0.138 mmol) and FeCl3.6H2O (3.7 mg, 0.014
mmol), in CH2Cl2 (3 ml) were used to furnish the product 14t (42 mg, 95%) as a yellow oil. Rf = 0.3
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(EtOAc-hexane 10:90); IR (neat): vmax/cm-1 2927, 1661, 1609, 1449, 1250, 1198, 1017; H NMR (400
MHz, CDCl3) δ 2.09 (br. s., Hz, 3H), 2.34 (s, 3H), 2.52 (dd, J = 16.8, 10.9 Hz, 1H), 3.68 (dd, J = 17.0,
3.8 Hz, 1H), 3.85 (s, 3H), 4.07 - 4.16 (m, 1H), 6.18 - 6.25 (m, 1H), 6.75 (d, J = 16.3 Hz, 1H), 6.98 (d, J
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