1480
M. Ishihara, H. Togo / Tetrahedron 63 (2007) 1474–1480
gel (CHCl /Et N¼10:1) to give pure 2-(4-methylphenyl)
Harman, W. D. J. Am. Chem. Soc. 2002, 124, 15099;
(e) Evans, D. A.; Downey, C. W.; Hubbs, J. L. J. Am. Chem.
Soc. 2003, 125, 8706; (f) Bhor, S.; Anilkumar, G.; Tse,
M. K.; Klawonn, M.; D €o bler, C.; Bitterlich, B.; Grotevendt,
A.; Beller, M. Org. Lett. 2005, 7, 3393; (g) Du, H.; He, Y.;
Sivappa, R.; Lovely, C. J. Synlett 2006, 965.
3
3
imidazoline.
4.5. Typical procedure for preparation of 2-oxazolines
from alcohols
To a solution of 4-methylbenzyl alcohol (122.2 mg, 1 mmol)
in tert-butyl alcohol (8 ml) were added K CO (552.8 mg,
3. (a) Ferm, R. J.; Riebsomer, J. L. Chem. Rev. 1954, 54, 593; (b)
Mohammadpoor-Baltork, I.; Khosropour, A. R.; Hojati, S. F.
Synlett 2005, 2747; (c) Mirkhani, V.; Moghadam, M.;
Tangestaninejad, S.; Kargar, H. Tetrahedron Lett. 2006, 47,
2129; (d) De la Hoz, A.; Diaz-Ortiz, A.; Mateo, M. D. C.;
Moral, M.; Moreno, A.; Elguero, J.; Foces-Foces, C.;
Rodriguez, M. L.; Sanchez-Migallon, A. Tetrahedron 2006,
62, 5868; (e) Wu, J.; Sun, X.; Xia, H. Tetrahedron Lett. 2006,
47, 1509; (f) Anastassiadou, M.; Baziard-Mouysset, G.;
Payard, M. Synthesis 2000, 1814.
2
3
4
mmol) and I (761.4 mg, 3 mmol). The obtained mixture
2
ꢀ
was stirred at 70 C. After 8 h, aminoethanol (91.6 mg,
.5 mmol) in tert-butyl alcohol (2 ml) was added to the re-
1
action mixture and stirred for another 18 h. The reaction
mixture was quenched with satd aq Na SO until the iodine
color almost disappeared, and was extracted with Et O. The
2
3
2
organic layer was washed with aq NaHCO , brine, and dried
3
over Na SO . After filtration, the solvent was removed in
2
4
vacuo. The residue was chromatographed on neutral silica
gel (AcOEt) to give 137.0 mg of the pure 2-(4-methylphenyl)-
oxazoline in 85% yield.
4. For examples, see: (a) Hughey, J. L., IV; Knapp, S.; Schugar, H.
Synthesis 1980, 489; (b) Quaglia, W.; Bousquet, P.; Pigini, M.;
Carotti, A.; Carrieri, A.; Dontenwill, M.; Gentili, F.; Giannella,
M.; Maranca, F.; Piergentili, A.; Brasili, L. J. Med. Chem. 1999,
4
2, 2737; (c) Neef, G.; Eder, U.; Sauer, G. J. Org. Chem. 1981,
46, 2824; (d) Mitchell, J. M.; Finney, N. S. Tetrahedron Lett.
000, 41, 8431; (e) You, S.; Kelly, J. W. Org. Lett. 2004, 6,
Acknowledgements
2
Financial support from a Grant-in-Aid for Scientific
Research (No. 16655012) from the Ministry of Education,
Science, Sports, and Culture of Japan, and Forum of Iodine
Utilization is gratefully acknowledged.
1681; (f) Aidouni, A.; Demonceau, A.; Delaude, L. Synlett
2006, 493.
5. (a) Vorbr €u ggen, H.; Krolikiewicz, K. Tetrahedron 1993, 49,
9353; (b) Cwik, A.; Hell, Z.; Heged €u s, A.; Finta, Z.; Horvath,
Z. Tetrahedron Lett. 2002, 43, 3985; (c) Bandgar, B. P.;
Pandit, S. S. Tetrahedron Lett. 2003, 44, 2331; (d) Whelligan,
D. K.; Bolm, C. J. Org. Chem. 2006, 71, 4609; (e) Kangani,
C. O.;Kelley, D. E.; Day, B. N. Tetrahedron Lett. 2006, 47, 6497.
6. Katritzky, A. R.; Cai, C.; Suzuki, K.; Singh, S. K. J. Org. Chem.
2004, 69, 811.
7. Badiang, J. G.; Aub ꢀe , J. J. Org. Chem. 1996, 61, 2484.
8. Huh, D. H.; Ryu, H.; Kim, Y. G. Tetrahedron 2004, 60, 9857.
9. Fujioka, H.; Murai, K.; Ohba, Y.; Hiramatsu, A.; Kita, Y.
Tetrahedron Lett. 2005, 46, 2197.
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67; (j) Brage, A. L.; L €u dtke, D. S.; Vargas, F.; Braga, R. C.
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2
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