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Paper | Regular issue | Vol 36, No. 8, 1993, pp.1803-1808
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6364
Synthesis of 5-Aryl-3-hydroxy-4H-pyran-4-ones

Hisashi Takao,* Yoshinori Endo, and Tokunaru Horie

*Naruto Research Center, Otsuka Chemical Company, Ltd., S atoura,Naruto 772, Japan


The palladium-catalyzed coupling reaction of 3-benzyloxy-5-bromo-2-methyl-4H-pyran-4-one (2b) with phenylboronic acid afforded efficiently 3-benzyloxy-2-methyl-5-phenyl-4H-pyran-4-one (3b-1), and the benzyloxy group of the resultant product was cleaved by hydrolysis with conc. hydrochloric acid in acetic acid to give 5-phenyl-3-hydroxy-2-methyl-4H-pyran-4-one (4b-1) in high yield. This method was applicable as a general method for synthesizing 5-aryl-3-hydroxy-4H-pyran-4-ones (4) from the 5-bromo-4H-pyran-4-ones (1).