Synthesis of 6-oxononanolides, 6-and 7-oxodecanolides and 7-oxoundecanolide via enamine reactions

IJ Borowitz, GJ Williams, L Gross…

Index: Borowitz,I.J. et al. Journal of Organic Chemistry, 1968 , vol. 33, # 5 p. 2013 - 2020

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Citation Number: 42

Abstract

Alkylation of the pyrrolidine enamines of several cyclohexanones with 3-bromopropyl acetate gives the corresponding 2-(3'-acetoxypropyl) cyclohexanones. These keto esters are hydrolyzed to keto alcohols which are cyclized and dehydrated to tetrahydrochromans. Alkylation of pyrrolidinocyclohexene or pyrrolidinocycloheptene with 4-bromobutyl acetate gives the corresponding 2-(4'-acetoxybutyl) cycloalkanone which is converted similarly ...