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Synlett 2011(6): 857-861  
DOI: 10.1055/s-0030-1259681
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Selective Synthesis of 2-Aryl-2H- and 4-Aryl-4H-3,5-diformylpyrans from Acetal with Aromatic Aldehydes Catalyzed by Lewis Acids

Norihide Horikawa, Yasushi Obora*, Yasutaka Ishii*
Department of Chemistry and Materials Engineering, Faculty of Chemistry, Materials and Bioengineering and ORDIST, Kansai University, Suita, Osaka 564-8680, Japan
Fax: +81(6)63394026; e-Mail: obora@kansai-u.ac.jp; e-Mail: r091001@kansai-u.ac.jp;
Further Information

Publication History

Received 21 January 2011
Publication Date:
22 February 2011 (online)

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Abstract

A selective method for 2-aryl-2H- and 4-aryl-4H-3,5-diformylpyrans synthesis from 1,1,3,3-tetramethoxypropane and aromatic aldehydes was developed using an FeCl3 catalyst in MeOH-AcOH and an AlCl3 catalyst in DMA-AcOH.

Key words

acetals - pyrans - aldehydes - Lewis acids - catalysis

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9

All the attempts to isolate or fully characterize the intermediates B, C, and D were unsuccessful. However, when the reaction of 1 and 2g was carried out at r.t. under the conditions as in Table  [²] , entry 7, the intermediate B for the formation of 3g was detected by GC and GC-MS analysis. HRMS (EI): m/z calcd for C11H7O2F3 [M]+: 228.0398; found: 228.0396.