[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[O:8])[CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[F:15][C:16]([Si](C)(C)C)([F:18])[F:17].O>CN(C)C=O.C(OCC)(=O)C>[F:15][C:16]([F:18])([F:17])[CH:7]([C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[OH:8]
3-Pyridinecarboxaldehyde (200 μL, 2.12 mmol) and potassium carbonate (58.6 mg, 0.424 mmol) were suspended in N,N-dimethylformamide (4.0 mL). To this, (trifluoromethyl)trimethylsilane (940 μL, 3.63 mmol) was added dropwise under a nitrogen atmosphere at room temperature and the mixture was stirred at the same temperature for 1.5. After water was added to the reaction mixture, extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure and the residue was dissolved in tetrahydrofuran (4.0 mL). To this, a 1 mol/L aqueous hydrogen chloride solution (5.0 mL) was added at room temperature and the mixture was stirred at the same temperature for 10 minutes. Then, the reaction mixture was neutralized with a saturated aqueous sodium bicarbonate solution, and extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/methanol=9/1) to give 3-(2,2,2-trifluoro-1-hydroxyethyl) pyridine (Compound CB) (341 mg, yield: 91%).
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