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Synthesis and aikylation of CIS ‐α‐hydroxyisopropylindanone‐2‐carboxylic acid lactone
Author(s) -
Campaigne E.,
Frierson Manton R.
Publication year - 1979
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.5570160207
Subject(s) - chemistry , hydrolysis , yield (engineering) , adduct , alkaline hydrolysis , alkylation , ring (chemistry) , carboxylic acid , acid hydrolysis , lactone , iodide , methyl iodide , organic chemistry , molecule , medicinal chemistry , catalysis , materials science , metallurgy
The Meldrum's acid adduct of isobutyrophenone was cyclized directly and in high yield to the title compound, which could then be alkylated at the 2‐position with methyl iodide or ethyl 6‐bromohexanoate. In the latter case, acid hydrolysis of the resultant ester gave the analogous acid, but alkaline hydrolysis resulted in ring opening of the indanone portion of the molecule.