A Short and Efficient Synthesis of 4,5-Disubstituted-1-pentenes
- 1 January 1986
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1986 (04) , 309-312
- https://doi.org/10.1055/s-1986-31594
Abstract
A one step synthesis of 5-chloro-4-hydroxy-1-pentene(65%) and 5-bromo-4-hydroxy-1-pentene (81%) was developed. Treatment of epibromohydrin or epichlorohydrin at -73°C with a reagent prepared from vinylmagnesium bromide and a catalytic amount of copper(I) bromide gave the desired products. 5-Bromo-4-hydroxy-1-pentene was cleanly converted to 4.5-epoxy-1-pentene in 99% yield by treatment with potassium hydroxide. A number of derivatives of 5-bromo-4-hydroxy-1-pentene are described.Keywords
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