The Journal of Organic Chemistry
Page 14 of 21
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Naphthalen-2-yl(phenyl)methanone (Table 2, 3u):18a eluent, hexane/ethyl acetate (99:1), (90
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mg, 78%). H NMR (300 MHz, CDCl3): δ = 8.28 (d, J = 1.2 Hz, 1H), 7.99 ꢀ 7.90 (m, 3H), 7.86
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(ddd, J = 8.1, 4.6, 2.1 Hz, 2H), 7.67 ꢀ 7.58 (m, 2H), 7.58 ꢀ 7.51 (m, 2H), 7.51 ꢀ 7.44 (m, 2H); C
NMR (75 MHz, CDCl3): δ = 196.9, 138.1, 135.4, 135.0, 132.5, 132.4, 132.0, 130.2, 129.6, 128.5,
128.0, 126.9, 126.0, 121.3, 118.7.
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(4-Chlorophenyl)(p-tolyl)methanone (Table 3, 4b):18c eluent, hexane/ethyl acetate (98:2), (85
mg, 74%). 1H NMR (300 MHz, CDCl3): δ = 7.80 ꢀ 7.61 (m, 4H), 7.53 ꢀ 7.39 (m, 2H), 7.39 ꢀ 7.21
(m, 2H), 2.44 (s, 3H); 13C NMR (75 MHz, CDCl3): δ = 195.4, 143.7, 138.7, 136.4, 134.7, 131.5,
130.3, 129.2, 128.7, 21.8.
(4-Methoxyphenyl)(p-tolyl)methanone (Table 3, 4c):18c eluent, hexane/ethyl acetate (98:2), (99
mg, 88%).1H NMR (300 MHz, CDCl3): δ = 7.97 ꢀ 7.74 (m, 2H), 7.74 ꢀ 7.62 (m, 2H), 7.37 ꢀ 7.21
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(m, 2H), 7.03 ꢀ 6.88 (m, 2H), 3.88 (s, 3H), 2.43 (s, 3H); C NMR (75 MHz, CDCl3): δ = 195.5,
163.2, 142.7, 135.6, 132.5, 130.6, 130.1, 129.0, 113.6, 55.6, 21.7.
(4-Bromophenyl)(p-tolyl)methanone (Table 3, 4d):18g eluent, hexane/ethyl acetate (99:1), (111
mg, 81%). 1H NMR (300 MHz, CDCl3): δ = 7.69 (d, J = 8.0 Hz, 2H), 7.66 ꢀ 7.57 (m, 4H), 7.30
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(s, 1H), 7.27 (d, J = 4.4 Hz, 1H), 2.45 (s, 3H); C NMR (75 MHz, CDCl3): δ = 195.5, 143.7,
136.8, 134.6, 131.7, 131.6, 130.3, 129.2, 127.3, 21.8.
Bis(4-methoxyphenyl)methanone (Table 3, 4h):18a eluent, hexane/ethyl acetate (97:3), (107
mg, 89%). 1H NMR (300 MHz, CDCl3): δ = 8.21 ꢀ 8.00 (m, 4H), 7.10 ꢀ6.87 (m, 4H), 3.89 (d, J
= 5.6 Hz, 6H); 13C NMR (75 MHz, CDCl3): δ = 171.5, 133.0, 132.5, 114.3, 113.9, 55.6.
(4-Chlorophenyl)(4-methoxyphenyl)methanone (Table 3, 4i):18h eluent, hexane/ethyl acetate
(98:2), (87 mg, 71%).1H NMR (300 MHz, CDCl3): δ = 8.14 (d, J = 8.4 Hz, 1H), 7.80 (d, J = 8.5
Hz, 1H), 7.71 (d, J = 8.1 Hz, 1H), 7.45 (d, J = 8.3 Hz, 1H), 7.38 (d, J = 8.6 Hz, 1H), 7.15 (d, J =
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8.4 Hz, 1H), 7.05 ꢀ 6.93 (m, 2H), 3.90 (s, 3H); C NMR (75 MHz, CDCl3): δ = 163.5, 136.7,
132.6, 132.5, 131.7, 131.3, 131.2, 123.0, 129.6, 128.7, 123.3, 114.1, 113.8, 55.7.
Phenyl(thiophen-2-yl)methanone (Table 3, 4p):16a eluent, hexane/ethyl acetate (98:2), (82 mg,
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88%). H NMR (300 MHz, CDCl3): δ = 7.94 ꢀ 7.82 (m, 2H), 7.73 (dd, J = 5.0, 1.1 Hz, 1H),
7.65 (dd, J = 3.8, 1.1 Hz, 1H), 7.63 ꢀ 7.56 (m, 1H), 7.50 (dd, J = 8.2, 6.6 Hz, 2H), 7.17 (dd, J =
4.9, 3.8 Hz, 1H); 13C NMR (75 MHz, CDCl3): δ = 188.4, 143.8, 138.3, 135.0, 134.4, 132.4,
129.3, 128.6, 128.1.
2,2,6,6-Tetramethylpiperidin-1-yl benzoate (Table 5, 5b):18i eluent, hexane/ethyl acetate
(98:2), (88 mg, 68%, based on 0.5 mmol scale). 1H NMR (300 MHz, CDCl3) δ = 8.40 (d, J = 7.4
Hz, 2H), 7.83 (d, J = 31.9 Hz, 3H), 2.28 – 1.71 (m, 7H), 1.58 (d, J = 8.5 Hz, 6H), 1.43 (d, J = 8.7
Hz, 5H). 13C NMR (75 MHz, DMSOꢀd6) δ = 163.1, 132.5, 128.3, 127.6, 127.1, 57.6, 37.3, 30.1,
19.2, 15.3.
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