Glycol monoethyl ether → 3-Ethoxy-4-(2-ethoxyethoxy)-2-methylpyridine

Participants

Reaction Steps

Triphenylphosphine (2.93 g, 11.2 mmol) was added to a stirred solution of 3-ethoxy-2-methylpyridin-4(1H)-one (1.42 g, 9.3 mmol, obtained from Example 4(b)) in THF (15 mL). 2-Ethoxy ethanol (2.93 g, 11.2 mmol) was added dropwise, followed by dropwise addition of DEAD (1.76 mL, 11.2 mmol). The reaction mixture was then stirred under reflux overnight. The solvent was evaporated in vacuo and the residue was dissolved in water (15 mL). The aqueous solution was adjusted to pH 1 with 2M hydrochloric acid, then extracted with ethyl acetate (3×20 mL). The combined organic phases were dried (MgSO4) and concentrated, and the crude product was purified by flash chromatography (CHCl3/MeOH; 9:1), giving the title compound (0.92 g, 44%).

Provenance & Evidence