Br[C:2]1[CH:3]=[C:4]([CH:8]2[O:13][CH2:12][CH2:11][CH2:10][O:9]2)[CH:5]=[CH:6][CH:7]=1.[Mg].[F:15][C:16]([F:24])([F:23])[C:17](=[O:22])[CH:18]=[C:19]([CH3:21])[CH3:20]>C1COCC1.[Cu]I>[O:9]1[CH2:10][CH2:11][CH2:12][O:13][CH:8]1[C:4]1[CH:3]=[C:2]([C:19]([CH3:21])([CH3:20])[CH2:18][C:17](=[O:22])[C:16]([F:24])([F:23])[F:15])[CH:7]=[CH:6][CH:5]=1A solution of the Grignard reagent (generated from the reaction of 2-(3-bromophenyl)-[1,3]dioxane with magnesium turnings in THF, 0.25 M, 52.6 mL, 13.1 mmol) was treated with copper (I) iodide (2.5 g, 13.1 mmol) at 0° C. After 45 minutes, 1,1,1-trifluoro-4-methylpent-3-en-2-one (2 g, 13.1 mmol) was added, and the reaction mixture was slowly warmed to room temperature and stirred overnight. The mixture was quenched with aqueous saturated ammonium chloride solution and extracted with ethyl acetate. The combined organic layers were washed with aqueous saturated sodium chloride solution, dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was triturated with hexanes and filtered. The filtrate was concentrated in vacuo to give 1.78 g of the crude product, which was used without purification.
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