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Synthesis 2007(10): 1584-1586
DOI: 10.1055/s-2007-965954
DOI: 10.1055/s-2007-965954
PSP
© Georg Thieme Verlag Stuttgart · New York
Simple and Efficient Preparation of Reagents for Thiopyran Introduction:
Methyl Tetrahydro-4-oxo-2H-thiopyran-3-carboxylate, Tetrahydro-4H-thiopyran-4-one, and 3,6-Dihydro-4-trimethylsilyloxy-2H-thiopyran
Further Information
Publication History
Received
4 October 2006
Publication Date:
28 February 2007 (online)


Abstract
Tetrahydro-4H-thiopyran-4-one was prepared in >75% yield by treatment of dimethyl 3,3′-thiobispropanoate with NaOMe (generated in situ) in THF solution and decarboxylation of the resulting methyl tetrahydro-4-oxo-2H-thiopyran-3-carboxylate in refluxing 10% aqueous H2SO4. Reaction of tetrahydro-4H-thiopyran-4-one with Me3SiCl and Et3N in CHCl3 gave the corresponding trimethylsilyl enol ether in near quantitative yield. The prepared reagents are useful for the synthesis of thiopyran-containing compounds.
Key words
tetrahydro-4H-thiopyran-4-one - 4-thianone - heterocyclic ketone - Dieckmann cyclization - thiopyran synthesis