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Synthese von 2‐Hydeoxy‐3‐methyl‐2‐hexen‐4‐olid
Author(s) -
Stach Hans,
Huggenberg Walter,
Hesse Manfred
Publication year - 1987
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19870700214
Subject(s) - chemistry , decarboxylation , yield (engineering) , hydrolysis , isomerization , medicinal chemistry , organic chemistry , stereochemistry , catalysis , materials science , metallurgy
Synthesis of 2‐Hydroxy‐3‐methyl‐2‐hexen‐4‐olid The title compound 13a, a substance used in food‐flavoring, was synthesized in 89% overall yield, starting from methyl 2‐hydeoxy‐3‐butenoate (3 a ). The key step in this transformation is the isomerization of the CC bond in 3 a which yielded methyl 2‐oxobutanoate as an intermediate. The latter underwent a self‐condensation yielding 2‐hydroxy‐4‐(methoxycarbonyl)‐3‐methyl‐2‐hexen‐4‐olid ( 11 a ), which, after hydrolysis and decarboxylation, gave 13 a . In addition, the syntheses of five other compounds related to 13 a are reported.