Page 15 of 23
The Journal of Organic Chemistry
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1H NMR (500 MHz, CDCl3) δ 8.01 (d, J = 2.0 Hz, 1H), 7.83 (dd, J = 8.4, 2.0 Hz, 1H), 7.65–7.55 (m, 3H), 7.32 (d,
J = 8.1 Hz, 2H), 4.87 (dd, J = 10.9, 3.5 Hz, 1H), 2.45 (s, 3H), 2.20–2.10 (m, 1H), 2.08–1.98 (m, 1H), 0.87 (t, J =
7.4 Hz, 3H); 13C NMR (125 MHz, CDCl3) δ 190.7, 145.7, 138.8, 136.9, 133.6, 133.2, 130.9, 130.8, 129.7, 129.6,
128.0, 71.9, 21.8, 21.7, 11.5; HRMS (ESI) calcd for C17H16Cl2O3SNa+ ([M + Na]+): 393.0089, found 393.0098.
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1-p-tolyl-2-tosylpropan-1-one (2i). Obtained as a white solid (70.6 mg, 78%); m.p. 104–105 C; H NMR (500
MHz; CDCl3): δ 7.88 (d, J = 7.8 Hz, 2H), 7.65 (d, J = 7.8 Hz, 2H), 7.31–7.26 (m , 4H), 5.13 (q, J = 6.6 Hz, 1H),
2.46–2.37 (m, 6H), 1.54 (d, J = 6.6 Hz, 3H); 13C NMR (125 MHz; CDCl3) δ 192.1, 145.3, 145.2, 133.9, 133.1,
129.8, 129.5, 129.4, 129.4, 64.9, 21.7, 21.7, 13.2; HRMS (ESI) calcd for C17H19O3S+ ([M + H]+): 303.1049, found
303.1049.
1-(2-methoxyphenyl)-2-tosylbutan-1-one (2j). Obtained as a white solid (84.3 mg, 88%); m.p. 106 – 107 C; 1H
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NMR (500 MHz, CDCl3) δ 7.63 (d, J = 8.3 Hz, 2H), 7.57 (dd, J = 7.7, 1.8 Hz, 1H), 7.47–7.42 (m, 1H), 7.24 (d, J =
8.1 Hz, 2H), 6.99–6.93 (m, 1H), 6.89 (d, J = 8.4 Hz, 1H), 5.47 (dd, J = 10.0, 4.3 Hz, 1H), 3.87 (s, 3H), 2.39 (s, 3H),
2.15–2.03 (m, 2H), 0.98 (t, J = 7.4 Hz, 3H); 13C NMR (125 MHz, CDCl3) δ 194.5, 158.4, 144.8, 134.5, 134.5,
131.1, 129.5, 129.3, 128.3, 120.9, 111.8, 75.1, 55.6, 21.6, 21.6, 11.6; HRMS (ESI) calcd for C18H21O4S+ ([M + H]+):
333.1155, found 333.1142.
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1-(3,4-dimethoxyphenyl)-2-tosylbutan-1-one (2k). Obtained as a white solid (88.7 mg, 83%); m.p. 163–164 C;
1H NMR (500 MHz, CDCl3) δ 7.66 (d, J = 8.1 Hz, 3H), 7.51 (s, 1H), 7.31 (d, J = 8.1 Hz, 2H), 6.92 (d, J = 8.4 Hz,
1H), 4.94 (dd, J = 10.9, 3.5 Hz, 1H), 3.97 (s, 3H), 3.94 (s, 3H), 2.44 (s, 3H), 2.20–2.10(m, 1H), 2.07–1.95 (m, 1H),
0.87 (t, J = 7.4 Hz, 3H); 13C NMR (125 MHz, CDCl3) δ 190.7, 154.3, 149.2, 145.2, 133.6, 130.7, 129.8, 129.4,
124.5, 110.6, 110.1, 71.1, 56.2, 56.0, 22.1, 21.7, 11.5; HRMS (ESI) calcd for C19H23O5S+ ([M + H]+): 363.1261,
found 363.1261.
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3-methyl-1-phenyl-2-tosylbutan-1-one (2l). Obtained as a white solid (58.4 mg, 62%); m.p. 81–82 C; H NMR
(500 MHz; CDCl3) δ 7.81 (d, J = 7.3 Hz, 2H), 7.70 (d, J = 8.3 Hz, 2H), 7.54 (t, J = 7.4 Hz, 2H), 7.43–7.39 (m, 2H),
7.23 (d, 8.1 Hz, 2H), 4.87 (d, J = 9.1 Hz, 1H), 2.60–2.49 (m, 1H), 2.36 (s, 3H), 1.33 (d, J = 6.6 Hz, 3H), 0.89 (d, J
= 6.6 Hz, 3H); 13C NMR (125 MHz; CDCl3) δ 193.9, 145.0, 137.8, 135.1, 133.6. 129.8, 129.4, 128.7, 128.6, 76.3,
29.6, 21.5, 21.4, 21.0; HRMS (ESI) calcd for C18H21O3S+ ([M + H]+): 317.1206, found 317.1207.
1-(4-bromophenyl)-4-chloro-2-tosylbutan-1-one (2m). Obtained as a white solid (97.2 mg, 78%); m.p. 145–146
oC; 1H NMR (500 MHz, CDCl3) δ 7.83 (d, J = 8.7 Hz, 2H), 7.60 (t, J = 8.5 Hz, 4H), 7.29 (d, J = 8.0 Hz, 2H), 5.35
(dd, J = 8.1, 5.8 Hz, 1H), 3.73–3.60 (m, 1H), 3.40–3.26 (m, 1H), 2.62–2.49 (m, 2H), 2.43 (s, 3H); 13C NMR (125
MHz, CDCl3) δ 190.9, 145.9, 135.5, 133.2, 132.1, 130.6, 129.8, 129.8, 129.6, 67.4, 41.6, 30.5, 21.7; HRMS (ESI)
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