Page 11 of 18
The Journal of Organic Chemistry
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2-((4-isobutyl-2-phenyloxazol-5-yl)oxy)-1-phenylethan-1-one. The product 3b was
obtained as a white solid (31.8 mg, 95%), m.p. 71.2ꢀ72.6 °C. IR (ZnSe, cmꢀ1): 3060,
2960, 2929, 2873, 1693, 1596, 1481, 1445, 1349, 1226, 984, 751, 718, 689, 844. 1H NMR
(500 MHz, CDCl3) δ 8.08 (d, J = 7.0 Hz, 2H), 8.02 (d, J = 7.9 Hz, 2H), 7.67 (t, J = 7.4
Hz, 1H), 7.55 (t, J = 7.7 Hz, 2H), 7.44 – 7.36 (m, 3H), 5.61 (s, 2H), 2.57 (d, J = 7.3 Hz,
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2H), 2.29 – 2.20 (m, 1H), 1.01 (d, J = 6.6 Hz, 6H). C{1H} NMR (125 MHz, CDCl3) δ
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190.8, 161.3, 157.6, 134.4, 134.2, 131.1, 129.1, 129.0, 128.4, 128.2, 126.4, 54.3, 34.9,
27.9, 22.4. HRMS (ESIꢀQTOF) m/z: [M + Na] + calcd for C21H21NO3Na 358.1419, found
358.1415.
2-((4-isopropyl-2-phenyloxazol-5-yl)oxy)-1-phenylethan-1-one. The product 3c was
obtained as a white solid (30.8 mg, 96%), m.p. 145.6ꢀ148.2 °C. IR (ZnSe, cmꢀ1): 3063,
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2972, 2936, 2863, 1688, 1596, 1496, 1453, 1348, 1223, 838, 748, 680. H NMR (500
MHz, CDCl3) δ 8.08 (d, J = 6.9 Hz, 2H), 8.02 (d, J = 8.0 Hz, 2H), 7.66 (t, J = 7.5 Hz,
1H), 7.54 (t, J = 7.9 Hz, 2H), 7.44 – 7.33 (m, 3H), 5.62 (s, 2H), 2.90 (sept, J = 6.8 Hz,
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1H), 1.39 (d, J = 6.9 Hz, 6H). C{1H} NMR (125 MHz, CDCl3) δ 191.0, 162.8, 161.3,
134.3, 134.2, 131.3, 129.1, 128.9, 128.4, 128.1, 126.4, 54.2, 26.0, 21.4. HRMS (ESIꢀ
QTOF) m/z: [M + Na] + calcd for C20H19NO3Na 344.1257, found 344.1247.
2-((4-(sec-butyl)-2-phenyloxazol-5-yl)oxy)-1-phenylethan-1-one. The product 3d was
obtained as a white solid (28.2 mg, 84%), m.p. 88.8ꢀ91.9 °C. IR (ZnSe, cmꢀ1): 3063,
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2962, 2924, 2870, 1690, 1595, 1479, 1448, 1346, 1222, 986, 746, 684. H NMR (500
MHz, CDCl3) δ 8.08 (d, J = 7.2 Hz, 2H), 8.02 (d, J = 7.6 Hz, 2H), 7.66 (t, J = 7.2 Hz,
1H), 7.54 (t, J = 7.5 Hz, 2H), 7.42 – 7.36 (m, 3H), 5.67 (d, J = 17.8 Hz, 1H), 5.58 (d, J =
17.8 Hz, 1H), 2.70 – 2.60 (sex, J = 6.9 Hz,1H), 1.96 – 1.87 (m, 1H), 1.75 – 1.67 (m, 1H),
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1.37 (d, J = 6.8 Hz, 3H), 0.90 (t, J = 7.3 Hz, 3H). C{1H} NMR (125 MHz, CDCl3) δ
191.0, 162.2, 161.4, 134.3, 134.3, 131.3, 129.1, 128.9, 128.4, 128.2, 126.2, 54.2, 33.1,
28.9, 19.3, 12.0. HRMS (ESIꢀQTOF) m/z: [M + Na] + calcd for C21H21NO3Na 358.1419,
found 358.1406.
2-((4-benzyl-2-phenyloxazol-5-yl)oxy)-1-phenylethan-1-one. The product 3e was obtained
as a white solid (33.5 mg, 91%) using the general procedure with concentration of 0.2
mol L−1 of azlactone in fluorobenzene, m.p. 159.7ꢀ161.2 °C. IR (ZnSe, cmꢀ1): 3080, 3059,
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3026, 2977, 2936, 1692, 1596, 1479, 1438, 1348, 1226, 841, 761, 716, 691. H NMR
(500 MHz, CDCl3) δ 8.11 (d, J = 7.0 Hz, 2H), 7.86 (d, J = 7.9 Hz, 2H), 7.64 (t, J = 7.3
Hz, 1H), 7.49 (t, J = 7.7 Hz, 2H), 7.46 – 7.36 (m, 3H), 7.30 – 7.16 (m, 5H), 5.37 (s, 2H),
4.22 (s, 2H). 13C{1H} NMR (125 MHz, CDCl3) δ 190.7, 161.2, 156.2, 135.0, 134.3,
134.1, 130.9, 129.1, 129.0, 128.9, 128.6, 128.5, 128.0, 127.2, 126.3, 54.8, 32.7. HRMS
(ESIꢀQTOF) m/z: [M + Na] + calcd for C24H19NO3Na 392.1257, found 392.1261.
2-((4-allyl-2-phenyloxazol-5-yl)oxy)-1-phenylethan-1-one. The product 3f was obtained
as a light orange solid (27.3 mg, 86%), m.p. 126.7ꢀ128.0 °C. IR (ZnSe, cmꢀ1): 3067,
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2982, 2922, 1696, 1592, 1475, 1446, 1345, 1221, 922, 724, 684. H NMR (500 MHz,
CDCl3) δ 8.08 (d, J = 7.2 Hz, 2H), 7.99 (d, J = 7.5 Hz, 2H), 7.66 (t, J = 7.2 Hz, 1H), 7.54
(t, J = 7.5 Hz, 2H), 7.45 – 7.35 (m, 3H), 6.01 – 5.94 (m, 1H), 5.62 (s, 2H), 5.17 (d, J
=10.1 Hz, 1H), 5.13 (d, J =17.21 Hz, 1H), 3.58 (d, J = 5.8 Hz, 2H). 13C{1H} NMR (125
MHz, CDCl3) δ 190.8, 161.3, 155.5, 134.4, 134.2, 131.7, 130.9, 129.1, 128.5, 128.1,
126.3, 118.3, 54.6, 30.9. HRMS (ESIꢀQTOF) m/z: [M + Na] + calcd for C20H17NO3Na
342.1101, found 342.1084.
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