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Thioalkylation of Enolates, IV. α‐Alkylidenecyclopentanones by α‐Alkylidation of Methyl 2‐Oxocyclopentanecarboxylate
Author(s) -
Arnecke Ralf,
Groth Ulrich,
Köhler Thomas
Publication year - 1994
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199419940908
Subject(s) - chemistry , saponification , zinc , cyclopentanone , reagent , flue gas desulfurization , dabco , alkali metal , organic chemistry , yield (engineering) , ketone , halide , magnesium , catalysis , materials science , metallurgy
An α‐alkylidation of cyclopentanone was achieved in two reaction steps in an overall yield of 20 to 79% via a zinc chloride‐catalyzed thioalkylation of the zinc enolate of methyl 2‐oxocyclopentanecarboxylate ( 3 ) and subsequent saponification/desulfurization of the β‐(phenylthio) ketone intermediates 5 . For the saponification/desulfurization step DABCO proved to be the reagent of choice and superior to the use of alkali or magnesium halides.