Direct and selective syntheses of alpha,alpha-dichloroethyl ketones or their ethyl trimethylsilyl mixed acetals by the reactions of methoxymethyl or ethyl carboxylates with 1,1-dichloroethyllithium in the presence of chlorotrimethylsilane

1,1-Dichloroethyllithium (1), generated by treating 1,1 dichloroethane (2) with lithium diisopropylamide (LDA) or n-butyllithium, reacted with methoxymethyl carboxylates in the coexistence of chlorotrimethylsilane (3) to afford the corresponding alpha,alpha-dichloroethyl ketones in good yields. On t...

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Bibliographic Details
Published inChemistry letters no. 9; pp. 1062 - 1063
Main Authors Shiina, Imai, Y, Suzuki, M, Yanagisawa, M, Mukaiyama, T
Format Journal Article
LanguageEnglish
Published TOKYO Chemical Soc Japan 01.09.2000
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
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Summary:1,1-Dichloroethyllithium (1), generated by treating 1,1 dichloroethane (2) with lithium diisopropylamide (LDA) or n-butyllithium, reacted with methoxymethyl carboxylates in the coexistence of chlorotrimethylsilane (3) to afford the corresponding alpha,alpha-dichloroethyl ketones in good yields. On the other hand, 1 reacted with ethyl carboxylates under the above reaction conditions to give 2,2-dichloro-1-alkyl-1-ethoxy-1-(trimethylsiloxy)propanes selectively in good yields.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.2000.1062