Abstract
Reaction of 4′,4′-dimethyl-3,4,5,8-tetrahydrospiro[2H-1-benzopyran-2,2′-[l,3]dioxolan](9) with methylmagnesium iodide in benzene or toluene at 40� gave the iodomagnesium enolate acetal (10) which upon in situ reaction with methyl iodide afforded 56% of pure 6 ξ-methyl- 6-[2′-(2″,4″,4″-trimethyl-1″,3″-dioxolan 2″yl)ethyl]cyclohex-3-en-one (11), the product of tandem nucleophilic/electrophilic dimethylation . Aqueous ammonium chloride workup of the iodomagnesium enolate
(10) gave 6-[2′-(2″,4″,4″-trimethyl-1″,3″-dioxolan 2″yl)ethyl] cyclohex-3-en-1-one (7). Some further transformations of the methylated keto acetal (11) are described.
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10 articles.
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