Y. Kawano, H. Togo / Tetrahedron 65 (2009) 6251–6256
6255
4.4.6. 2-Methyl-4-heptyl-5-phenyloxazole
Oil. IR (neat): 2930, 2860, 1720, 1240, 760, 690 cmꢂ1
(400 MHz, CDCl3): ¼1.20–1.43 (m, 8H),
¼0.87 (t, J¼6.9 Hz, 3H),
1.72 (m, 2H),
1H), 7.42 (t, J¼7.4 Hz, 2H), 7.56 (d, J¼7.4 Hz, 2H). MS (FAB): m/z¼258
[MþH]. HRMS: calcd for C17H24NO: 258.1858; found: 250.1864.
(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
.
1H NMR
d
d
C12H13N2O3: 233.0926; found: 233.0927.
d
¼2.49 (s, 3H), 2.60 (t, J¼7.9 Hz, 2H), 7.30 (t, J¼7.4 Hz,
4.4.16. 2-Propyl-5-(40-methylphenyl)oxazole
Oil. IR (neat): 3130, 1700, 1500, 810 cmꢂ1
CDCl3):
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.
.
1H NMR (400 MHz,
d
¼1.03 (t, J¼7.5 Hz, 3H), 1.85 (m, 2H), 2.37 (s, 3H), 2.80 (t,
4.4.7. 2-Ethyl-5-phenyloxazole
Oil. IR (neat): 3060, 2980, 2940, 1580, 1560, 1490, 1450, 760,
690 cmꢂ1. 1H NMR (400 MHz, CDCl3):
(q, J¼7.6 Hz, 2H), 7.22 (s, 1H), 7.30 (tt, 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.
d
¼1.40 (t, J¼7.6 Hz, 3H), 2.86
4.4.17. 2-Propyl-4-methyl-5-phenyloxazole
Oil. IR (neat): 2970, 1700, 1570, 1020, 760, 690 cmꢂ1
.
1H NMR
¼2.41
¼7.42 (t,
(400 MHz, CDCl3):
(s, 3H),
¼2.78 (t, J¼7.6 Hz, 2H),
J¼7.5 Hz, 2H),
d
¼1.03 (t, J¼7.3 Hz, 3H),
d
¼1.85 (m, 2H),
d
4.4.8. 2-Ethyl-5-(40-chlorophenyl)oxazole
d
d¼7.30 (t, J¼7.5 Hz, 1H),
d
Oil. IR (neat): 1570, 1560, 1490, 1130, 1090, 820 cmꢂ1
.
1H NMR
d
¼7.58 (d, J¼7.5 Hz, 2H). MS (FAB): m/z¼202 [MþH].
(400 MHz, CDCl3):
d
¼1.38 (t, J¼7.7 Hz, 3H), 2.85 (q, J¼7.7 Hz, 2H),
HRMS: m/z [MþH] calcd for C13H16NO: 202.1226; found: 202.1226.
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.
4.4.18. 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,
4.4.9. 2-Ethyl-5-(40-nitrophenyl)oxazole
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.
Mp 81–82 ꢁC (lit.13 mp 85–86 ꢁC). IR (KBr): 3120, 2990, 1620,
1560, 1500, 1330, 750 cmꢂ1. 1H NMR (400 MHz, CDCl3):
d¼1.42 (t,
J¼7.6 Hz, 3H), 2.90 (q, J¼7.6 Hz, 2H), 7.44 (s, 1H), 7.76 (d, J¼9.0 Hz,
2H), 8.28 (d, J¼9.0 Hz, 2H).
4.4.19. 2-Isopropyl-5-(40-chlorophenyl)oxazole
Oil. IR (neat): 2970, 1550, 1490, 1090, 820 cmꢂ1 1H NMR
.
4.4.10. 2-Ethyl-5-(40-methylphenyl)oxazole
(400 MHz, CDCl3):
d¼1.40 (d, J¼7.7 Hz, 6H), 3.15 (septet, J¼7.7 Hz,
Mp 54–55 ꢁC (lit.15 mp 56–57 ꢁC). IR (KBr): 1580, 1560, 1500,
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.
1460, 1380 cmꢂ1
.
1H NMR (400 MHz, CDCl3):
d¼1.40 (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.
4.4.20. 2-Isopropyl-5-(40-nitrophenyl)oxazole
Mp 52–53 ꢁC. IR (Nujol): 1580, 1460, 1350, 850 cmꢂ1 1H NMR
.
4.4.11. 2-Ethyl-4-methyl-5-phenyloxazole
(400 MHz, CDCl3):
d
¼1.43 (d, J¼7.1 Hz, 6H), 3.20 (septet, J¼7.1 Hz,
Oil. IR (neat): 1570, 1500, 1240, 1020, 760, 690 cmꢂ1
.
1H NMR
1H), 7.44 (s, 1H), 7.77 (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.
(400 MHz, CDCl3):
d
¼1.38 (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.
4.4.21. 2-Isopropyl-5-(40-methylphenyl)oxazole
Oil. IR (neat): 2970, 1700, 1560, 1510, 810 cmꢂ1 1H NMR
.
4.4.12. 2-Ethyl-4-heptyl-5-phenyloxazole
(400 MHz, CDCl3):
d
¼1.39 (d, J¼7.3 Hz, 6H), 2.40 (s, 3H), 3.11 (sep-
Oil. IR (neat): 2960, 2930, 2860, 1460, 760, 690 cmꢂ1
.
1H NMR
tet, J¼7.3 Hz,1H), 7.28 (t, J¼7.3 Hz,1H), ¼7.42 (t, J¼7.9 Hz, 2H), 7.58
d
(400 MHz, CDCl3):
d¼0.89 (t, J¼7.9 Hz, 3H), 1.20–1.45 (m, 11H), 1.72
(d, J¼7.9 Hz, 2H). MS (FAB): m/z¼202 [MþH]. HRMS: m/z [MþH]
(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.
calcd for C13H16NO: 202.1226; found: 202.1226.
4.4.22. 2-Isopropyl-4-methyl-5-phenyloxazole
Oil. IR (neat): 2970, 1560, 760, 690 cmꢂ1 1H NMR (400 MHz,
.
CDCl3):
d
¼1.38 (d, J¼7.0 Hz, 6H), 2.40 (s, 3H), 3.10 (septet, J¼7.0 Hz,
4.4.13. 2-Propyl-5-phenyloxazole
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; found: 202.1226.
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.
4.4.23. IL-supported PhI D
Mp 99–100 ꢁC. IR (Nujol): 1440, 1380, 1160, 840, 820, 750,
560 cmꢂ1. 1H NMR (400 MHz, Acetone-d6):
2H), 7.19 (d, J¼8.5 Hz 2H), 7.63 (d, J¼3.4 Hz, 1H), 7.66 (d, J¼3.4 Hz,
1H), 7.70 (d, J¼8.5 Hz, 2H), 9.00 (s, 1H). E.A Calcd for C11H12F6IN2P:
C, 29.75; H, 2.72; N, 6.31; found: C, 29.88; H, 2.49; N, 6.28.
d
¼3.95 (s, 3H), 5.45 (s,
4.4.14. 2-Propyl-5-(40-chlorophenyl)oxazole
Mp 29–30 ꢁC. IR (Nujol): 1560, 1490, 1460, 1020, 1090, 820 cmꢂ1
.
1H NMR (400 MHz, CDCl3):
d
¼1.04 (t, J¼7.3 Hz, 3H), 1.85 (m, 2H),
2.80 (t, J¼7.6 Hz, 2H), 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.
Acknowledgements
4.4.15. 2-Propyl-5-(40-nitrophenyl)oxazole
Financial support in the form of a Grant-in-Aid for Scientific
Research (No. 2003/007) from the Ministry of Education, Culture,
Sports, Science, and Technology, Japan is gratefully acknowledged.
Mp 74–75 ꢁC. IR (Nujol): 1610, 1510, 1460, 1330, 850 cmꢂ1 1H
.
NMR (400 MHz, CDCl3):
d¼1.05 (t, J¼7.4 Hz, 3H), 1.88 (m, 2H), 2.85