Water → 2,2,2-Trifluoro-1-(pyridin-3-yl)ethanol

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%).

1. washby washing with brine
2. dry with materialdrying over anhydrous sodium sulfate
3. customThe solvent was evaporated off under reduced pressure
4. dissolutionthe residue was dissolved in tetrahydrofuran (4.0 mL)
5. additionTo this, a 1 mol/L aqueous hydrogen chloride solution (5.0 mL) was added at room temperature
6. stirringthe mixture was stirred at the same temperature for 10 minutes
7. extractionThen, the reaction mixture was neutralized with a saturated aqueous sodium bicarbonate solution, and extraction with ethyl acetate
8. washby washing with brine
9. dry with materialdrying over anhydrous sodium sulfate
10. customThe solvent was evaporated off under reduced pressure
11. customthe residue was purified by silica gel column chromatography (chloroform/methanol=9/1)

ORD record

ord-b862c1e5b8cb4301b673a342759b5a2b

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08673908B2