Method for preparing 4-hydroxy-3-methyl-2-(2-propynyl)-2-cyclope

Details Method for preparing 4-hydroxy-3-methyl-2-(2-propynyl)-2-cyclope Method for preparing 4-hydroxy-3-methyl-2-(2-propynyl)-2-cyclope

1980-06-16

1982-08-10

Trousof, Natalie

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

560176, 568396, 568390, 568413, C07C 4545

Patent

active

043439535

ABSTRACT:
The present invention relates to a novel method for producing cyclopentenolone of the formula (I), ##STR1## which is a useful intermediate for producing agricultural chemicals, which comprises reacting an acetonedicarboxylic ester of the formula (VII), ##STR2## wherein R is a C.sub.1 -C.sub.6 alkyl group, with 2-propynyl chloride in the presence of magnesium alkoxide and in the presence of alkali iodide to obtain novel mono-(2-propynyl)-substituted acetonedicarboxylic ester of the formula (VI), ##STR3## wherein R is as defined above; hydrolyzing the mono-(2-propynyl)-substituted acetonedicarboxylic ester of the formula (VI) under alkaline conditions with an alkali and then reacting the hydrolyzed product with methylglyoxal of the formula, ##STR4## to obtain novel .gamma.-diketone of the formula (V), ##STR5## and ring-closing the .gamma.-diketone of the formula (V) under alkaline condition.

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patent: 4173707 (1979-11-01), Torii et al.
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Kurono et al., Chem. Abst., vol. 90, #86704a (1979).
Ite et al., Chem. Abst., vol. 91, #56450t (1979).
Muramoto et al., Chem. Abst., vol. 79, #41727s (1973).
Muramoto et al., Chem. Abst., vol. 82, #139218p (1975).
Calame et al., Chem. Abst., vol. 80, #3172v (1974).

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