[F:1][C:2](=[CH:5][C:6]([F:9])([F:8])[F:7])[CH2:3][OH:4].C([O-])(=O)C.[Na+].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.CCOCC>C(Cl)Cl>[F:1]/[C:2](=[CH:5]\[C:6]([F:9])([F:8])[F:7])/[CH:3]=[O:4]To the solution of 2,4,4,4-tetrafluoro-2-butenol (1.40 g) and anhydrous sodium acetate (60 mg) in methylene chloride (5 ml) was added in portionwise pyridinium chlorochromate (3.23 g) at 20° C. The resulting mixture was stirred for 12 hours. The mixture was passed through a short silica gel column with dry ether (20 ml) to obtain the ether solution of (Z)-2,4,4,4-tetrafluoro-2-butenal. Without evaporation, a tetrahydrofuran solution of ethynylmagnesium bromide (21 ml) was added portionwise to the solution of (Z)-2,4,4,4-tetrafluoro-2-butenal at 0° C. The resulting mixture was stirred for 12 hours at 20° C. This was poured into the cooled 5% hydrochloric acid, and the resulting mixture was extracted with ether. The ether extract was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate.
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