Chloromethyl Methyl Ether → 4-[1-(Trifluoromethyl)-1-(methoxymethoxy)-2,2,2-trifluoroethyl]styrene

A solution of 1,1,1,3,3,3-hexafluoro-2-(4-vinylphenyl)-2-propanol (5.00 g, 18.51 mmol) in THF (10 mL)was slowly added to a mixture of NaH (60% dispersion, 968 mg, 24.20 mmol), washed with pentane, and THF (50 mL). The reaction mixture was allowed to stir at room temperature for 1 h, then cooled to −78° C. using a dry ice/acetone bath followed by the addition of chloromethyl methyl ether (1.50 mL, 19.75 mmol) in THF (5 mL). The reaction mixture was allowed to slowly warm to room temperature overnight, quenched with H2O, concentrated, and partitioned between ether/H2O. The combined extracts were washed with saturated NaHCO3, brine, dried (Na2SO4), and concentrated to provide a crude oil. This material was purified by Kugelrohr distillation (bp 65-9° C., 1.3 mm), followed by column chromatography on silica gel using 50:1 hexane/ethyl acetate to provide 1.96 g (34%) of a colorless oil; 1H NMR (CDCl3) δ 7.60 (d, 2ArH), 7.50 (d, 2ArH), 6.75 (dd, CH=), 5.85 (dd ═CHH), 5.40 (dd ═CHH), 4.85 (s, CH2), 3.60 (s, Me).