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
I. Shiina et al., 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, CHEM LETT, (9), 2000, pp. 1062-1063
1,1-Dichloroethyllithium (1), generated by treating 1,1 dichloroethane (2)
with lithium diisopropylamide (LDA) or n-butyllithium, reacted with methoxy
methyl carboxylates in the coexistence of chlorotrimethylsilane (3) to affo
rd the corresponding alpha,alpha-dichloroethyl ketones in good yields. On t
he other hand, 1 reacted with ethyl carboxylates under the above reaction c
onditions to give 2,2-dichloro-1-alkyl-1-ethoxy-1-(trimethylsiloxy)propanes
selectively in good yields.