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A New Synthesis of 2‐(6‐Methoxycarbonylhexyl)‐Cyclopent‐2‐ EN ‐1‐One Using α‐Silylallyl Sulphide
Author(s) -
Chen LingChing,
Wu ShihnSheng
Publication year - 1985
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.198500076
Subject(s) - chemistry , aluminium chloride , chloride , acylation , condensation , hydrolysis , aldol condensation , aluminium , medicinal chemistry , catalysis , organic chemistry , physics , thermodynamics
Acylation of the α‐trimethylsilylallyl phenyl sulphide (2). by reaction with the acid chloride (3), catalyzed by aluminium chloride in CH 2 Cl 2 at −78° C , gave methyl 9‐oxo‐12‐phenylthio‐11‐dodecene (4). Hydrolysis of (4) followed by aldol condensation gave 2‐(6‐methoxycarbonylhexyl)‐cyclopent‐2‐ en ‐1‐one (6).