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Sur l'hydrolyse acide du méthoxy‐1‐hexène‐1‐yne‐3 et du méthoxy‐1‐hexadiène‐1,3. Synthèse de pyrazoles substitués et du cis ‐hexène‐3‐al
Author(s) -
Winter M.
Publication year - 1963
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.19630460531
Subject(s) - chemistry , phenylhydrazine , hydrolysis , hydrazine (antidepressant) , medicinal chemistry , pyrazole , stereochemistry , organic chemistry , biochemistry
Acid hydrolysis of 1‐methoxy‐1‐hexene‐3‐yne (I) gives as main product the unstable β‐oxohexanal, and not β‐hexynal as suggested earlier by Herbertz. The mechanism of this reaction is briefly discussed. Acid hydrolysis of I in the presence of phenylhydrazine yields a mixture of two 1‐phenyl‐prophylpyrazoles. With hydrazine, 3‐propyl‐pyrazole is obtained. This reaction is of general interest for the synthesis of 3‐substituted pyrazoles.