Synthese de la trifluoromethyl-vinyl-cetone

The synthesis of trifluoromethylvinylketone $\text{6}$ is described. The metal hydride reduction of ethyl trifluoroacetoacetate $\text{1}$ gives the glycol $\text{2}$. Selective tosylation of $\text{2}$ occurs on the primary hydroxyl group and leads to $\text{3}$. Tosyl-chloride exchange produces the chlorohydrin $\text{4}$ which is oxydized to the β chloroketone $\text{5}$. The dehydrohalogenation of $\text{5}$ leads to the fluorinated ethylenic ketone $\text{6}$.