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H. Jiang et al.
PAPER
3-Butyl-5-methyl-4-methylene-5-phenyloxazolidin-2-one (3h)
IR (KBr): 2957, 2870, 1760, 1667 cm–1.
Orange-red oil.
IR (KBr): 2933, 2867, 1760 cm–1.
1H NMR (400 MHz, CDCl3): d = 0.88–0.93 (m, 3 H), 1.29–1.34 (m,
2 H), 1.55–1.60 (m, 2 H), 1.85 (s, 3 H), 3.42–3.51 (m, 2 H), 4.08 (d,
J = 2.8 Hz, 1 H), 4.21 (d, J = 3.2 Hz, 1 H), 7.31–7.45 (m, 5 H).
1H NMR (400 MHz, CDCl3): d = 0.93–0.97 (m, 3 H), 1.36–1.41 (m,
2 H), 1.61–1.67 (m, 2 H), 2.27 (s, 3 H), 3.59 (t, J = 7.4 Hz, 2 H),
7.35–7.47 (m, 5 H).
13C NMR (100 MHz, CDCl3): d = 9.4, 13.6, 19.9, 31.3, 41.6, 118.7,
124.9, 127.4, 128.7, 134.1, 155.0.
13C NMR (100 MHz, CDCl3): d = 13.6, 20.1, 27.5, 28.3, 41.3, 82.0,
91.4, 124.8, 127.8, 128.6, 141.2, 149.7, 155.6.
MS (EI, 70 eV): m/z (%) = 231 [M+] (100), 175 (88), 105 (25), 77
(13), 42 (11), 28 (28).
MS (EI, 70 eV): m/z (%) = 245 [M+] (20), 190 (22), 158 (100), 144
(100), 129 (32), 97 (65), 77 (23), 41 (8).
Anal. Calcd for C14H17NO2: C, 72.70; H, 7.41; N, 6.06. Found: C,
72.57; H, 7.34; N, 6.04.
Anal. Calcd for C15H19NO2: C, 73.44; H, 7.81; N, 5.71. Found: C,
73.19; H, 8.01; N, 5.46.
3-Butyl-4-methyl-5-pentyloxazol-2 (3H)-one (4c)
Orange-red oil.
3-Butyl-5-isopropyl-5-methyl-4-methyleneoxazolidin-2-one (3i)
IR (KBr): 2955, 2866, 1756, 1685 cm–1.
Orange-red oil.
IR (KBr): 2968, 2876, 1775, 1673 cm–1.
1H NMR (400 MHz, CDCl3): d = 0.87–0.99 (m, 9 H), 1.30–1.36 (m,
2 H), 1.43 (s, 3 H), 1.53–1.57 (m, 2 H), 1.80–1.82 (m, 1 H), 3.31–
3.38 (m, 1 H), 3.43–3.57 (m, 1 H), 3.91 (d, J = 2.8 Hz, 1 H), 4.08
(d, J = 2.8 Hz, 1 H).
13C NMR (100 MHz, CDCl3): d = 13.7, 16.1, 20.0, 24.9, 28.3, 41.1,
79.5, 86.6, 149.4, 156.2.
MS (EI, 70 eV): m/z (%) = 211 [M+] (32), 169 (90), 126 (29), 112
1H NMR (400 MHz, CDCl3): d = 0.84–0.93 (m, 6 H), 1.22–1.33 (m,
6 H), 1.49–1.58 (m, 4 H), 1.92 (s, 3 H), 2.30 (t, J = 7.2 Hz, 2 H),
3.45 (t, J = 7.4 Hz, 2 H).
13C NMR (100 MHz, CDCl3): d = 7.9, 13.6, 13.9, 19.8, 22.3, 24.3,
27.2, 31.0, 31.3, 41.5, 117.0, 135.3, 155.8.
MS (EI, 70 eV): m/z (%) = 225 [M+] (40), 168 (100), 112 (90), 41
(11).
Anal. Calcd for C13H23NO2: C, 69.29; H, 10.29; N, 6.22. Found: C,
69.09; H, 10.14; N, 6.22.
(100), 84 (10), 55 (14), 41 (22).
3-Butyl-5-isopropyl-4-methyloxazol-2 (3H)-one (4d)
Orange-red oil.
IR (KBr): 2966, 2873, 1754, 1698 cm–1.
Anal. Calcd for C12H21NO2: C, 68.21; H, 10.02; N, 6.63. Found: C,
67.89; H, 10.09; N, 6.30.
3-Butyl-5-hexyl-5-methyl-4-methyleneoxazolidin-2-one (3j)
Dark-red oil.
IR (KBr): 2929, 2863, 1675 cm–1.
1H NMR (400 MHz, CDCl3): d = 0.89 (t, J = 7.4 Hz, 3 H), 1.12 (t,
J = 9.4 Hz, 6 H), 1.30–1.35 (m, 2 H), 1.54–1.66 (m, 2 H), 2.71–2.75
(m, 1 H), 3.45 (t, J = 7.4 Hz, 2 H).
1H NMR (400 MHz, CDCl3): d = 0.84 (t, J = 6.8 Hz, 3 H), 0.92 (t,
J = 7.2 Hz, 3 H), 1.23–1.34 (m, 10 H), 1.44–1.64 (m, 5 H), 3.41 (m,
2 H), 3.90 (d, J = 2.8 Hz, 1 H), 4.07 (d, J = 2.8 Hz, 1 H).
13C NMR (100 MHz, CDCl3): d = 13.7, 14.0, 20.0, 22.5, 22.8, 26.9,
28.3, 29.1, 31.6, 40.8, 79.1, 84.4, 149.8, 156.0.
13C NMR (100 MHz, CDCl3): d = 7.8, 13.6, 19.9, 20.8, 24.9, 31.3,
41.4, 115.1, 139.5, 155.7.
MS (EI, 70 eV): m/z (%) = 197 [M+] (41), 182 (89), 141 (11), 126
(100), 44 (6), 42 (13).
Anal. Calcd for C11H19NO2: C, 66.97; H, 9.71; N, 7.10. Found: C,
66.71; H, 9.74; N, 7.15.
MS (EI, 70 eV): m/z (%) = 253 [M+] (5), 169 (100), 126 (25), 113
(30), 98 (38), 55 (10), 41 (12).
3-Butyl-4-methyloxazol-2 (3H)-one (4e)
Orange oil.
IR (KBr): 2958, 2971, 1749, 1662 cm–1.
Anal. Calcd for C15H27NO2: C, 71.10; H, 10.74; N, 5.53. Found: C,
70.83; H, 10.62; N, 5.37.
3-Butyl-4,5-dimethyloxazol-2 (3H)-one (4a)
Orange oil.
IR (KBr): 2954, 2872, 1756, 1706 cm–1.
1H NMR (400 MHz, CDCl3): d = 0.91 (q, J = 4.9 Hz, 3 H), 1.30–
1.36 (m, 2 H), 1.55–1.72 (m, 2 H), 1.99 (s, 3 H), 3.49 (t, J = 7.4 Hz,
2 H), 6.52 (q, J = 1.6 Hz, 1 H).
1H NMR (400 MHz, CDCl3): d = 0.91 (t, J = 7.4 Hz, 3 H), 1.28–1.35
(m, 2 H), 1.53–1.59 (m, 2 H), 1.91 (s, 3 H), 1.99 (s, 3 H), 3.46 (t,
J = 3.8 Hz, 2 H).
13C NMR (100 MHz, CDCl3): d = 7.8, 9.7, 13.5, 19.7, 31.2, 41.4,
117.0, 131.1, 155.6.
13C NMR (100 MHz, CDCl3): d = 8.7, 13.6, 19.8, 31.2, 41.4, 123.1,
123.9, 156.2.
MS (EI, 70 eV): m/z (%) = 155 [M+] (76), 126 (25), 99 (100), 85
(20), 42 (39).
Anal. Calcd for C8H13NO2: C, 61.91; H, 8.44; N, 9.03. Found: C,
61.88; H, 8.53; N, 8.98.
MS (EI, 70 eV): m/z (%) = 169 [M+] (90), 126 (29), 113 (100), 98
(42), 57 (12), 42 (36).
Anal. Calcd for C9H15NO2: C, 63.88; H, 8.93; N, 8.28. Found: C,
63.49; H, 9.06; N, 8.05.
Acknowledgments
The authors thank National Natural Science Foundation of China
(Nos. 20772034, 20625205, 20572027, and 20332030) and Guang-
dong Natural Science Foundation (No. 07118070) for the financial
support of this work.
3-Butyl-4-methyl-5-phenyloxazol-2 (3H)-one (4b)
Orange-red oil.
Synthesis 2008, No. 5, 763–769 © Thieme Stuttgart · New York