The Journal of Organic Chemistry
Page 12 of 15
3-(4-fluorophenyl)-2-(phenylthio)-1H-inden-1-one (20): red solid (41.9 mg, 63% yield), mp 131ꢀ133 oC.
1H NMR (500 MHz, CDCl3) δ 7.59ꢀ7.57 (m, 2H), 7.52 (d, J = 7.0 Hz, 1H), 7.40ꢀ7.37 (m, 1H), 7.30ꢀ7.24
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(m, 3H), 7.20ꢀ7.16 (m, 4H), 7.15ꢀ7.11 (m, 2H); C{1H} NMR (125 MHz, CDCl3) δ 193.0, 163.8 (d,
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1JCF = 250 Hz), 160.6, 144.4, 136.7, 134.5, 133.8, 131.1, 130.8 (d, JCF = 8.8 Hz), 129.6, 129.5, 129.4,
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129.1, 126.7, 123.6, 121.5, 115.9 (d, JCF =21.3 Hz); LRMS (EI, 70 eV) m/z (%): 332 (M+, 100), 183
(31), 239 (30), 331 (27), 255 (26); HRMS (ESI) calcd for C21H14FOS+ ([M + H]+): 333.0744, Found:
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333.0750.
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3-(4-chlorophenyl)-2-(phenylthio)-1H-inden-1-one (21): red solid (52.3 mg, 75% yield), mp 85ꢀ87 C.
1H NMR (500 MHz, CDCl3) δ 7.54ꢀ7.53 (m, 3H), 7.47ꢀ7.46 (m, 2H), 7.41ꢀ7.38 (m, 1H), 7.31ꢀ7.27 (m,
3H), 7.22ꢀ7.19 (m, 2H), 7.17ꢀ7.14 (m, 2H); C{1H} NMR (125 MHz, CDCl3) δ 192.8, 160.2, 144.2,
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136.7, 136.3, 134.3, 133.9, 131.0, 130.2, 130.0, 129.6, 129.1, 129.0, 128.1, 126.8, 123.7, 121.4; LRMS
(EI, 70 eV) m/z (%): 348 (M+, 100), 350 (41), 320, 284 (38), 163 (32); HRMS (ESI) calcd for
C21H14ClOS+ ([M + H]+): 349.0448, Found: 349.0452.
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3-cyclohexyl-2-(phenylthio)-1H-inden-1-one (22): yellow solid (20.5 mg, 32% yield), mp 90ꢀ92 C. H
NMR (500 MHz, CDCl3) δ 7.46 (d, J = 7.0 Hz, 1H), 7.41ꢀ7.38 (m, 2H), 7.29ꢀ7.26 (m, 3H), 7.25ꢀ7.22
(m, 2H), 7.16ꢀ7.13 (m, 1H), 3.22ꢀ3.16 (m, 1H), 1.97ꢀ1.86 (m, 4H), 1.82ꢀ1.75 (m, 3H), 1.43ꢀ1.34 (m,
3H); 13C{1H} NMR (125 MHz, CDCl3) δ 193.7, 172.3, 143.6, 135.9, 133.6, 131.5, 129.4, 129.1, 128.6,
126.2, 126.1, 123.1, 121.7, 39.9, 30.0, 26.3, 26.1; LRMS (EI, 70 eV) m/z (%): 320 (M+, 100), 143 (32),
115 (29), 321, 211 (24); HRMS (ESI) calcd for C21H21OS+ ([M + H]+): 321.1308, Found: 321.1308.
5-methyl-3-phenyl-2-(phenylthio)-1H-inden-1-one (23): red solid (46.0 mg, 70% yield), mp 130ꢀ132 oC.
1H NMR (500 MHz, CDCl3) δ 7.59ꢀ7.57 (m, 2H), 7.52ꢀ7.48 (m, 3H), 7.43 (d, J = 7.5 Hz, 1H), 7.28ꢀ7.26
(m, 2H), 7.22ꢀ7.18 (m, 2H), 7.15ꢀ7.12 (m, 1H), 7.10ꢀ7.08 (m, 1H), 7.01 (s, 1H), 2.36 (s, 3H); C{1H}
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NMR (125 MHz, CDCl3) δ 192.9, 161.8, 145.0, 144.8, 135.0, 132.0, 130.2, 129.5, 129.2, 129.0, 128.7,
128.6, 128.5, 127.7, 126.5, 123.7, 123.0, 22.2; LRMS (EI, 70 eV) m/z (%):328 (M+, 100), 300 (39), 329
(26), 327, 251 (23). HRMS (ESI) calcd for C22H17OS+ ([M + H]+): 329.0995, Found: 329.0993.
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5-ethyl-3-phenyl-2-(phenylthio)-1H-inden-1-one (24): red solid (43.1 mg, 63% yield), mp 119ꢀ121 C.
1H NMR (500 MHz, CDCl3) δ 7.59ꢀ7.58 (m, 2H), 7.53ꢀ7.48 (m, 3H), 7.46 (d, J = 7.5 Hz, 1H), 7.28ꢀ7.26
(m, 2H), 7.21ꢀ7.18 (m, 2H), 7.15ꢀ7.11 (m, 2H), 7.03 (s, 1H), 2.65 (q, J = 8.0 Hz, 2H), 1.23 (t, J = 8.0
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Hz, 3H); C{1H} NMR (125 MHz, CDCl3) δ 192.9, 161.9, 151.2, 145.0, 135.0, 132.0, 130.2, 129.2,
129.0, 128.9, 128.8, 128.6, 128.4, 127.7, 126.4, 123.8, 122.0, 26.9, 15.4; LRMS (EI, 70 eV) m/z (%):
342 (M+, 100), 314 (38), 313 (31), 343 (27), 299 (23); HRMS (ESI) calcd for C23H19OS+ ([M + H]+):
343.1151, Found: 343.1160.
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