New approach to 3,3-difluoroallyl alcohol

A new difluoroalkene with a triethylsilyl group, 4,4-difluoro-3-(triethylsilyl)- but-3-en-1-ol (1), was synthesized as a new building block for 1,1-difluoro-1-alkenes. Treatment of 1 with sodium hydride in the presence of a catalytic amount of p-methoxyphenol induced SiCsp2 bond dissociation. Subsequent addition of an aldehyde to the reactive intermediate afforded 3,3-difluoroallyl alcohol (9). The reaction was accelerated by added p-methoxyphenol.