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Paper | Regular issue | Vol 34, No. 5, 1992, pp.1047-1054
Published online, 1st January, 1970
DOI: 10.3987/COM-92-5997
Convenient Synthesis of 5-Trifluoromethyl-3-oxazolines and 5-Trifluoromethyloxazoles

Yasuhiro Kamitori, Masaru Hojo,* Ryoichi Masuda, Toshiya Takahashi, and Masaaki Wada

*Department of Industrial Chemistry, Faculty of Engineering, Kobe University, Kobe 657, Japan


Aldehyde tert-butyl(methyl)hydrazones were acylated with trifluoroacetic anhydride to afford 3-tert-butyl(methyl)hydrazono-1,1,1-trifluoroalkan-2-ones (4) in good yields. Several 5-hydroxy-5-trifluoromethyl-3-oxazolines (5) were successfully synthesized by thermally induced reaction of 4 adsorbed on silica gel. Treatment of 5 with POCl3/pyridine and subsequent dehydrochlorination with diisopropylethylamine gave 5-trifluoromethyloxazoles (6) in high yields.