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Synthesis 1986; 1986(4): 309-312
DOI: 10.1055/s-1986-31594
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A Short and Efficient Synthesis of 4,5-Disubstituted-1-pentenes

Ann De Camp Schuda* , Paul H. Mazzocchi, Gregory Fritz, Tina Morgan
  • *Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, U. S. A.
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Publication Date:
27 September 2002 (online)

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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.

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