Y. Ishiwata, H. Togo / Tetrahedron 65 (2009) 10720–10724
10723
d
¼1.40 (t, J¼7.6 Hz, 3H), 2.86 (q, J¼7.6 Hz, 2H), 7.22 (s, 1H), 7.30 (tt,
(t, J¼7.3 Hz, 3H),1.85 (m, 2H), 2.41 (s, 3H), 2.78 (t, J¼7.6 Hz, 2H), 7.30
(t, J¼7.5 Hz, 1H), 7.42 (t, J¼7.5 Hz, 2H), 7.58 (d, J¼7.5 Hz, 2H). MS
(FAB): m/z¼202 [MþH]. HRMS: m/z [MþH] calcd for C13H16NO:
202.1226; found: 202.1226.
J¼1.4, 7.6 Hz, 1H), 7.40 (dd, J¼7.6, 8.0 Hz, 2H), 7.61 (dd, J¼1.4, 8.0 Hz,
2H). HRMS: m/z [MþH] calcd for C11H12NO: 174.0919; found:
174.0922.
4.2.8. 2-Ethyl-5-(40-chlorophenyl)oxazole. Oil. IR (neat): 1570, 1560,
4.2.18. 2-Propyl-4-heptyl-5-phenyloxazole. Oil. IR (neat): 2928,
1490, 1130, 1090, 820 cmꢂ1
.
1H NMR (400 MHz, CDCl3):
d
¼1.38 (t,
2856, 1568, 1495, 1464, 1283, 1011, 764, 693 cmꢂ1 1H NMR
.
J¼7.7 Hz, 3H), 2.85 (q, J¼7.7 Hz, 2H), 7.20 (s, 1H), 7.37 (d, J¼8.5 Hz,
2H), 7.53 (d, J¼8.5 Hz, 2H). MS (FAB): m/z¼210 [MþH]. HRMS: m/z
[MþH] calcd for C12H12NOCl: 208.0529; found: 208.0521.
(400 MHz, CDCl3):
d¼0.87 (t, J¼6.8 Hz, 3H), 1.02 (t, J¼7.5 Hz, 3H),
1.21–1.45 (m, 8H), 1.72 (m, 2H), 1.84 (m, 2H), 2.71 (t, J¼8.0 Hz, 2H),
2.76 (t, J¼7.4 Hz, 2H), 7.29 (t, J¼7.5 Hz, 1H), 7.42 (t, J¼8.0 Hz, 2H),
7.56 (d, J¼7.0 Hz, 2H). HRMS: m/z [MþH] calcd for C19H28NO:
286.2171; found: 286.2160.
4.2.9. 2-Ethyl-5-(40-nitrophenyl)oxazole. Mp 81–82 ꢀC (lit.9 mꢂp185–
86 ꢀC). IR (KBr): 3120, 2990, 1620, 1560, 1500, 1330, 750 cm
.
1H
NMR (400 MHz, CDCl3):
2H), 7.44 (s, 1H), 7.76 (d, J¼9.0 Hz, 2H), 8.28 (d, J¼9.0 Hz, 2H).
d
¼1.42 (t, J¼7.6 Hz, 3H), 2.90 (q, J¼7.6 Hz,
4.2.19. 2-Isopropyl-5-phenyloxazole. Oil. IR (neat): 2970, 1560,
1240, 760, 690 cmꢂ1
.
1H NMR (400 MHz, CDCl3):
d
¼1.41 (d,
J¼7.0 Hz, 6H), 3.15 (septet, J¼7.0 Hz, 1H), 7.21 (s, 1H), 7.30 (t,
J¼7.5 Hz, 1H), 7.40 (t, J¼7.5 Hz, 2H), 7.62 (d, J¼7.5 Hz, 2H). MS (FAB):
m/z¼188 [MþH]. HRMS: m/z [MþH] calcd for C12H14NO: 188.1075;
found: 188.1068.
4.2.10. 2-Ethyl-5-(40-methylphenyl)oxazole. Mp 54–55 ꢀC (lit.11 mp
56–57 ꢀC). IR (KBr): 1580, 1560, 1500, 1460, 1380 cmꢂ1 1H NMR
(400 MHz, CDCl3):
.
d
¼1.40 (t, J¼7.6 Hz, 3H), 2.37 (s, 3H), 2.85 (q,
J¼7.6 Hz, 2H), 7.16 (s, 1H), 7.21 (d, J¼8.1 Hz, 2H), 7.49 (d, J¼8.1 Hz,
2H). MS (FAB) m/z¼188 [MþH]. HRMS: m/z [MþH] calcd for
C13H15NO: 188.1075; found: 188.1063.
4.2.20. 2-Isopropyl-5-(40-chlorophenyl)oxazole. Oil. IR (neat): 2970,
1550, 1490, 1090, 820 cmꢂ1. 1H NMR (400 MHz, CDCl3):
d
¼1.40 (d,
J¼7.7 Hz, 6H), 3.15 (septet, J¼7.7 Hz, 1H), 7.21 (s, 1H), 7.38 (t,
J¼8.8 Hz, 2H), 7.55 (t, J¼8.8 Hz, 2H). MS (FAB): m/z¼222 [MþH].
HRMS: m/z [MþH] calcd for C12H13NOCl: 222.0686; found:
222.0698.
4.2.11. 2-Ethyl-4-methyl-5-phenyloxazole. Oil. IR (neat): 1570, 1500,
1240, 1020, 760, 690 cmꢂ1
.
1H NMR (400 MHz, CDCl3):
d¼1.38 (t,
J¼7.6 Hz, 3H), 2.38 (s, 3H), 2.82 (q, J¼7.6 Hz, 2H), 7.29 (t, J¼8.0 Hz,
1H), 7.42 (t, J¼8.0 Hz, 2H), 7.58 (d, J¼8.0 Hz, 2H). MS (FAB):
m/z¼188 [MþH]. HRMS: m/z [MþH] calcd for C13H15NO: 188.1075;
found: 188.1073.
4.2.21. 2-Isopropyl-5-(40-nitrophenyl)oxazole. Mp 52–53 ꢀC. IR
(Nujol): 1580, 1460, 1350, 850 cmꢂ1 1H NMR (400 MHz, CDCl3):
.
d
¼1.43 (d, J¼7.1 Hz, 6H), 3.20 (septet, J¼7.1 Hz, 1H), 7.44 (s, 1H), 7.77
4.2.12. 2-Ethyl-4-heptyl-5-phenyloxazole. Oil. IR (neat): 2960, 2930,
(d, J¼8.0 Hz, 2H), 8.28 (d, J¼8.0 Hz, 2H). MS (FAB): m/z¼233 [MþH].
HRMS: m/z [MþH] calcd for C12H13N2O3: 233.0926; found:
233.0919.
2860, 1460, 760, 690 cmꢂ1
.
1H NMR (400 MHz, CDCl3):
d¼0.89 (t,
J¼7.9 Hz, 3H), 1.20–1.45 (m, 11H), 1.72 (m, 2H), 2.71 (t, J¼7.9 Hz, 2H),
2.82 (q, J¼7.6 Hz, 2H), 7.49 (t, J¼7.6 Hz, 1H), 7.42 (t, J¼7.6 Hz, 2H),
7.56 (d, J¼7.6 Hz, 2H). MS (FAB): m/z¼272 [MþH]. HRMS: m/z
[MþH] calcd for C18H25NO: 272.2014; found: 272.2013.
4.2.22. 2-Isopropyl-5-(40-methylphenyl)oxazole. Oil. IR (neat): 2970,
1700, 1560, 1510, 810 cmꢂ1. 1H NMR (400 MHz, CDCl3):
d¼1.39 (d,
J¼7.3 Hz, 6H), 2.40 (s, 3H), 3.11 (septet, J¼7.3 Hz, 1H), 7.28 (t,
J¼7.3 Hz, 1H), 7.42 (t, J¼7.9 Hz, 2H), 7.58 (d, J¼7.9 Hz, 2H). MS (FAB):
m/z¼202 [MþH]. HRMS: m/z [MþH] calcd for C13H16NO: 202.1226;
found: 202.1226.
4.2.13. 2-Propyl-5-phenyloxazole. Oil. IR (neat): 2970, 1560, 760,
690 cmꢂ1. 1H NMR (400 MHz, CDCl3):
d
¼1.04 (t, J¼7.3 Hz, 3H), 1.85
(m, 2H), 2.81 (t, J¼7.4 Hz, 2H), 7.22 (s, 1H), 7.30 (t, J¼7.5 Hz,1H), 7.40
(t, J¼7.5 Hz, 2H), 7.62 (d, J¼7.5 Hz, 2H). MS (FAB): m/z¼188 [MþH].
HRMS: m/z [MþH] calcd for C12H14NO: 188.1075; found: 188.1064.
4.2.23. 2-Isopropyl-4-methyl-5-phenyloxazole. Oil. IR (neat): 2970,
1560, 760, 690 cmꢂ1
.
1H NMR (400 MHz, CDCl3):
d¼1.38 (d,
4.2.14. 2-Propyl-5-(40-chlorophenyl)oxazole. Mp
(Nujol): 1560, 1490, 1460, 1020, 1090, 820 cmꢂ1. 1H NMR (400 MHz,
CDCl3):
7.22 (s, 1H), 7.38 (d, J¼8.6 Hz, 2H), 7.54 (d, J¼8.6 Hz, 2H). MS (FAB):
m/z¼222 [MþH]. HRMS: m/z [MþH] calcd for C12H13NOCl:
222.0686; found: 222.0697.
29–30 ꢀC.
IR
J¼7.0 Hz, 6H), 2.40 (s, 3H), 3.10 (septet, J¼7.0 Hz, 1H), 7.28 (t,
J¼7.8 Hz, 1H), 7.42 (t, J¼7.8 Hz, 2H), 7.54 (d, J¼7.8 Hz, 2H). MS (FAB):
m/z¼202 [MþH]. HRMS: m/z [MþH] calcd for C13H16NO: 202.1226.
d
¼1.04 (t, J¼7.3 Hz, 3H), 1.85 (m, 2H), 2.80 (t, J¼7.6 Hz, 2H),
4.2.24. 2,5-Diphenyloxazole. Mp 61 ꢀC (lit.12 mp 72 ꢀC). IR (Nujol):
1589, 1546, 1446, 1349, 1247, 1133, 1070, 1027, 953, 822, 758,
711 cmꢂ1. 1H NMR (400 MHz, CDCl3):
d¼7.35 (t, J¼7.5 Hz, 1H), 7.41–
4.2.15. 2-Propyl-5-(40-nitrophenyl)oxazole. Mp 74–75 ꢀC. IR (Nujol):
7.52 (m, 6H), 7.73 (d, J¼7.3 Hz, 2H), 8.12 (dd, J¼1.7, 8.1 Hz, 2H).
1610,1510,1460, 1330, 850 cmꢂ1. 1H NMR (400 MHz, CDCl3):
d
¼1.05
(t, J¼7.4 Hz, 3H), 1.88 (m, 2H), 2.85 (t, J¼7.5 Hz, 2H), 7.44 (s, 1H), 7.76
(d, J¼7.9 Hz, 2H), 7.58 (d, J¼7.9 Hz, 2H). MS (FAB): m/z¼233 [MþH].
HRMS: m/z [MþH] calcd for C12H13N2O3: 233.0926; found:
233.0927.
Acknowledgements
Financial support in the form of a Grant-in-Aid for Scientific
Research (No. 20550033) from the Ministry of Education, Culture,
Sports, Science, and Technology, Japan is gratefully acknowledged.
4.2.16. 2-Propyl-5-(40-methylphenyl)oxazole. Oil. IR (neat): 3130,
1700, 1500, 810 cmꢂ1
.
1H NMR (400 MHz, CDCl3):
d
¼1.03
References and notes
(t, J¼7.5 Hz, 3H),1.85 (m, 2H), 2.37 (s, 3H), 2.80 (t, J¼7.6 Hz, 2H), 7.16
(s, 1H), 7.21 (d, J¼8.0 Hz, 2H), 7.50 (d, J¼8.0 Hz, 2H). MS (FAB):
m/z¼202 [MþH]. HRMS: m/z [MþH] calcd for C13H16NO: 202.1226;
found: 202.1226.
1. (a) Comprehensive Heterocyclic Chemistry; Boyd, G. V., Katritzky, A. R., Rees, C. W.,
Eds.; Pergamon: Oxford, 1984; Vol. 6, Chapter 4.18; (b) Comprehensive Hetero-
cyclic Chemistry II; Hartner, F. W., Katritzky, A. R., Rees, C. W., Scriven, E. F. V.,
Eds.; Elsevier Science: Oxford, 1996; Vol. 3, Chapter 3.04; (c) Pattenden, G.
J. Heterocycl. Chem. 1992, 29, 607; (d) Michael, J. P.; Pattenden, G. Angew. Chem.,
Int. Ed. Engl. 1993, 32, 1; (e) Wipf, P. Chem. Rev. 1995, 95, 2115; (f) Vedejs, E.;
Monahan, S. D. J. Org. Chem. 1996, 61, 5192; (g) Brain, C. T.; Paul, J. M. Synlett
4.2.17. 2-Propyl-4-methyl-5-phenyloxazole. Oil. IR (neat): 2970,
1700, 1570, 1020, 760, 690 cmꢂ1. 1H NMR (400 MHz, CDCl3):
d
¼1.03