[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][N:3]=1.[F-].[Cs+].C[Si](C)(C)[C:14]([F:17])([F:16])[F:15].Cl>COCCOC.C1COCC1.O.C(OCC)(=O)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH:6]([OH:7])[C:14]([F:17])([F:16])[F:15])=[CH:8][CH:9]=1To a solution of 6-chloronicotinaldehyde (5.93 g, 41.9 mmol) and CsF (1.27 g, 8.38 mmol) in DME (350 mL) was added trimethyl(trifluoromethyl)silane (9.82 mL, 62.8 mmol) in THF (30 mL) at 0° C. The reaction mixture was allowed to warm to ambient temperature and the reaction was stirred at ambient temperature for 18 hours. 1 N HCl (50 mL) in water was added and the reaction was stirred at ambient temperature for 1 hour. Ethyl acetate (100 mL) was added. The organic layer was separated, washed with saturated sodium bicarbonate and brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (4:1 hexane/ethyl acetate) to give 1-(6-chloropyridin-3-yl)-2,2,2-trifluoroethanol (8.8 g, 99.3%) as an oil.
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