[F:1][C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([F:15])[C:13]=1F)[C:5]([O:7][CH2:8][C:9]#[CH:10])=[O:6].[CH2:16]([OH:19])[C:17]#[CH:18].CN(C=O)C.[H-].[Na+]>O>[F:15][C:12]1[CH:11]=[C:4]([CH:3]=[C:2]([F:1])[C:13]=1[O:19][CH2:16][C:17]#[CH:18])[C:5]([O:7][CH2:8][C:9]#[CH:10])=[O:6]To a mixture obtained by adding 5.0 g of 2-propynyl 3,4,5-trifluorobenzoate and 1.7 g of propargyl alcohol to 20 ml of DMF was added 1.1 g of 60% sodium hydride (oily) at 0° C. The resulting mixture was stirred at 0° C. for 30 minutes, and then at room temperature for 1 hour. Thereafter, water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and 2.9 g of 2-propynyl 3,5-difluoro-4-(2-propynyloxy)benzoate was obtained.
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