[Synthesis]
GENERAL STEPS: A mixture of potassium tert-butoxide (9.88 g, 88.07 mmol) and 2-chloropyridine (5 g, 44.04 mmol) was dissolved in toluene (100 mL), followed by the addition of 18-crown-6 (0.58 g, 2.20 mmol) as a phase transfer catalyst. The reaction mixture was stirred and refluxed at 110 °C for 15 hours. After completion of the reaction, the mixture was cooled to room temperature, diluted with ethyl acetate (200 mL) and washed sequentially with water (150 mL) and saturated brine (150 mL). The organic layer was separated, dried with anhydrous sodium sulfate and concentrated under reduced pressure to remove the solvent. The resulting crude product was purified by silica gel column chromatography using gradient elution (0:5 to 1:5 ethyl acetate/hexane) to afford the target compound 2-(tert-butoxy)pyridine (3.59 g, 54%) as a colorless oil. The structure of the product was confirmed by 1H NMR, 13C NMR and high resolution mass spectrometry (HRMS): 1H NMR (400 MHz, CDCl3) δ 8.15 (ddd, J = 4.8, 2.0, 0.4 Hz, 1H), 7.52 (ddd, J = 9.2, 6.8, 1.6 Hz, 1H), 6.81 (ddd, J = 6.8, 5.2, 1.2 Hz, 1H), 6.67 (dt, J = 8.4, 0.8 Hz, 1H), 1.61 (s, 9H); 13C NMR (100 MHz, CDCl3) δ 163.9, 146.5, 138.1, 116.2, 113.4, 79.4, 28.7 (3C); HRMS (ESI) m/z calcd for C9H14NO [M + H]+ 152.1075, found 152.1077. |