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Convenient synthesis of 5-alkylidene-2(5H)-furanones,2(5H)-furanones and 2-ethoxyfurans

โœ Scribed by R.W. Saalfrank; W. Hafner; J. Markmann; H.-J. Bestmann

Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
341 KB
Volume
44
Category
Article
ISSN
0040-4020

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โœฆ Synopsis

Starting fro enolizing 1.2~diketones 1 and (2,2dlathoxyvinylidene)triphenylphosphorane (1) or from 2 and (2.2-dlethoxyvlnyl)triphewlphosphonlu tetrafluorohorate (a) the orthoesters 2 are prepared. 9 can be hydrolyzed under acldlc conditions to glve 5-alkylldene-2(SH)-furan%es lo. Reaction of 1,2-hydroxyketones 11 and (2,2-dlethoxyvlnylldew)trIphenylphosphorane (2) vla Nlchael addition and Ylttlg reaction ytelds orthoesters 2. which can be hydrolyzed to give 2(5H)-furanones 16 and P-ethoxyfuranS 17 respectively. rconslderable variation of the substltuents (R') can be achieved starting from 11 and (2.2-d1ethoxyvlnyl)trlphenylphosphonlu tetrafluoroborates 2. -

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