PREPARATION OF BETA-HYDROXY ESTER

PURPOSE:To prepare the titled compound useful as an intermediate for organic syntheses, in high yield, by reacting an alpha-haloester with metallic tin and a carbonyl compound in a polar solvent, and hydrolyzing the reaction product. CONSTITUTION:The objective compound of formula III is prepared by...

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Bibliographic Details
Main Authors HARADA TAIRA, MUKOUYAMA MITSUAKI
Format Patent
LanguageEnglish
Published 24.01.1984
Subjects
ACYCLIC OR CARBOCYCLIC COMPOUNDS
CHEMISTRY
METALLURGY
ORGANIC CHEMISTRY
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Summary:PURPOSE:To prepare the titled compound useful as an intermediate for organic syntheses, in high yield, by reacting an alpha-haloester with metallic tin and a carbonyl compound in a polar solvent, and hydrolyzing the reaction product. CONSTITUTION:The objective compound of formula III is prepared by reacting the alpha-haloester of formula I (R and R are H, alkyl or aryl; R is alkyl or aryl; X is halogen) with metallic tin (e.g. active tin obtained by reducing stannous halide with aluminum lithium hydride) and the carbonyl compound of formula II (R and R are H, alkyl or aryl) in a polar solvent (e.g. ethanol) preferably at -100-+200 deg.C, and hydrolyzing the reaction product preferably at -78-+100 deg.C. The use of metallic tin enables the reduction of the content of steric isomers, and the preferential preparation of the erythro compound in high yield.
Bibliography:Application Number: JP19820123020