
%0 Journal Article
%A Collins, DJ 
%A James, AM 
%T Preparation of 2-(3-Bromo-1-methylpropyl)-1,3-dioxolan and the Corresponding Chloride From 2-Methylbutyrolactone
%J Australian Journal of Chemistry
%D 0989/01/01
%V 42
%N 1
%P 223-228
%K 
%R https://doi.org/10.1071/CH9890223
%U https://www.publish.csiro.au/paper/CH9890223 
%X Lithium aluminium hydride reduction of ethyl 4-chloro-2-methylbutanoate (4a), derived from 3-methyldihydrofuran-2(3H)-one (2-methylbutyrolactone) (1), gave 4-chloro-2-methylbutan-1-ol (5a), oxidation of which with pyridinium chlorochromate afforded 4-chloro-2-methylbutanal (8a). The aldehyde (8a) was converted into 2-(3&38242;-chloro-1&#8242;-methylpropyl)-1,3-dioxolan (7a) in 47% overall yield from (1). 2-(3&#8242;-Bromo-1&#8242;-methyIpropyl)-1,3-dioxolan (7b) was similarly obtained in 49% overall yield from (1). Attempted conversion of 3-methyltetrahydrofuran-2-ol (2) into the corresponding cyclic ethylene acetal gave epimeric mixtures of 2-(3&#8242;-methyltetrahydrofuran-2&#8242;-yloxy)ethanol (6) and 2,2&#8242;-ethylenedioxybis(3-methyltetrahydrofuran) (9). 
