[CH3:1][Si:2]([CH3:22])([CH3:21])[C:3]1[C:16]([F:17])=[C:15]([F:18])[C:6]([CH2:7][O:8]C2CCCCO2)=[C:5]([F:19])[C:4]=1[F:20].C(OCC)(=O)C.C(OCC)C>CO.Cl>[CH3:1][Si:2]([CH3:22])([CH3:21])[C:3]1[C:16]([F:17])=[C:15]([F:18])[C:6]([CH2:7][OH:8])=[C:5]([F:19])[C:4]=1[F:20]The crude tetrahydropyranyl ether prepared in Stage (i) was dissolved in methanol (20 cm3), and to the stirred solution was added concentrated hydrochloric acid (3 drops). After stirring for 16 hours at the ambient temperature (ca. 25° C.), the reaction mixture was poured into ethyl acetate, washed with water and brine, and dried. Evaporation of the solvent under reduced pressure gave a yellow oil which was subjected to column chromatography on silica gel using petroleum ether (boiling range 40°-60° C.) containing diethyl ether (10% gradually increased to 40% by volume) as eluent to give 4-trimethylsilyl-2,3,5,6-tetrafluorobenzyl alcohol (0.79 g).
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