[F:1][C:2]([Si:6]([CH3:17])([CH3:16])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH3:15])=[CH:9][CH:8]=1)=[C:3](F)[F:4].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.O>O1CCCC1.CCOCC.Cl>[F:1][C:2]([Si:6]([CH3:16])([CH3:17])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH3:15])=[CH:9][CH:8]=1)=[CH:3][F:4]
A solution of p-[(trifluorovinyl)dimethylsilyl]phenetole (12.0 g, 0.046 mol) in tetrahydrofuran is added dropwise to a stirred mixture of lithium aluminum hydride (1.75 g, 0.046 mol) in tetrahydrofuran at -5° C. The resultant reaction mixture is stirred at room temperature for 4 hours, cooled to 0° C., treated sequentially with ethyl acetate, water and dilute hydrochloric acid, and diluted with additional ether and dilute hydrochloric acid. The organic phase is separated, washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give the title product as a yellow liquid (10.76 g) which is identified by 1H NMR analysis as a 9:1 mixture of Z:E isomers.
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