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3‐[( Z )‐2‐ t ‐Butoxyethenyl]‐4‐hydroxy‐2(5 H )‐furanone, an interesting byproduct obtained from reaction of 4‐ t ‐butoxy‐2‐butenoate with the alkoxide anion of methyl glycolate
Author(s) -
Arora S. K.,
Cho B. S.,
Chadha V. K.,
Bauer A. J.,
Venton D. L.,
Lim C. T.,
Le Breton G. C.
Publication year - 1986
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570230362
Subject(s) - chemistry , alkoxide , medicinal chemistry , stereochemistry , organic chemistry , catalysis
Treatment of methyl 4‐ t ‐butoxy‐2‐butenoate ( 1 ) with the alkoxide anion of methyl glycolate gives, in addition to the previously reported (Fried, et al . [2]) 2,3‐disubstítuted‐2,3‐dihydro‐4‐furanone 2 , an equivalent amount of the interestingly substituted 3‐[( Z )‐2‐ t ‐butoxyethenyl]‐4‐hydroxy‐2(5 H )furanone 3 . Isolation, structure proof and possible mechanism of formation are presented