An improved procedure for the conversion of certain coumarins to 2,2-dimethylchromenes: efficient transformation of umbelliferone to precocene 1

An improved procedure for the conversion of certain coumarins to 2,2-dimethylchromenes: efficient transformation of umbelliferone to precocene 1

An improved method for transforming certain coumarins to 2,2-dimethylchromencs has been developed. Umbelliferone ( 1 b) was efficiently converted to precocene 1 ( 2 b) (73%) by etherification to herniarin ( 1 c) with tetramethylorthocarbonate, followed by reaction with methyllithium and cyclization...

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Veröffentlicht in:Canadian journal of chemistry 1983-09, Vol.61 (9), p.1963-1964
Hauptverfasser: Strunz, George M, Brillon, Denis, Giguère, Pierre
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
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Zusammenfassung:An improved method for transforming certain coumarins to 2,2-dimethylchromencs has been developed. Umbelliferone ( 1 b) was efficiently converted to precocene 1 ( 2 b) (73%) by etherification to herniarin ( 1 c) with tetramethylorthocarbonate, followed by reaction with methyllithium and cyclization of the resulting phenolic alcohol on silica gel.
ISSN:0008-4042
1480-3291
DOI:10.1139/v83-338