C([Li])CCC.[CH3:6][O:7][C:8]1[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[CH:10][N:9]=1.[CH:16](=[O:19])[CH2:17][CH3:18]>O1CCCC1>[CH3:6][O:7][C:8]1[C:13]([O:14][CH3:15])=[C:12]([CH:16]([OH:19])[CH2:17][CH3:18])[CH:11]=[CH:10][N:9]=1n-Butyllithium (38.7 mL; 10 M in tetrahydrofuran (THF)) was dissolved in THF (600 mL) and cannulated to a solution of 2,3-dimethoxypyridine (3) (22.4 g; 161 mmol) in THF (200 mL) at −78° C. The reaction mixture was then warmed to 0° C. and stirred for 1 hour. The propionaldehyde (29.1 mL; 403 mmol) was added dropwise at −78° C. The reaction mixture was warmed to 25° C. and stirred for 16 hours. The reaction mixture was subsequently quenched with water and extracted with dichloromethane. The combined extracts were dried over sodium sulfate, concentrated under reduced pressure and purified by chromatography (SiO2; 2-10% ethyl acetate/hexane) to give the 2,3-dimethoxy-4-(1′-hydroxypropyl)pyridine (4) product (18.6 g; 59%) as a colorless oil.
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