[CH3:1][C:2]([CH3:17])([O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]([F:16])([F:15])[F:14])=[CH:8][CH:7]=1)[C:3]#[CH:4].C([Li])CCC.[F:23][C:24]([F:31])([F:30])[C:25](OCC)=[O:26].CCCCCC.C(OCC)C>O1CCCC1.O>[F:23][C:24]([F:31])([F:30])[C:25](=[O:26])[C:4]#[C:3][C:2]([CH3:17])([O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]([F:14])([F:15])[F:16])=[CH:8][CH:7]=1)[CH3:1]
To a solution of 1.47 g (6 mmol) of 1-(1,1-dimethyl-2-propynyloxy)-4-trifluoromethoxybenzene in 25 ml of tetrahydrofuran cooled to -78° C. is added 2.4 ml of n-butyllithium (2.5M in hexanes). The solution is maintained with stirring for 1 hour. The mixture is treated with 1.70 g (12 mmol, 1.43 ml) of ethyl trifluoroacetate at -78° C. and is allowed to warm to room temperature. After stirring for 1 hour, the mixture is diluted with water and is extracted with ethyl ether (3 times). The combined ethereal extracts are washed with aqueous sodium bicarbonate, dried over magnesium sulfate, filtered and evaporated to give a light oil. Flash chromatography using hexane:ethyl ether (65:35) affords the title compound: IR (film) 2215, 1740 cm-1 ; NMR (CDCl3) δ1.73 (6H, s), 7.16 (4H, m).
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