Sodium hydride → Methyl 2-[2-(3,4-diethoxyphenyl)thiazole-4-ylmethyl]-3-(3-ethoxypyridine-2-yl)-3-oxopropionate

Participants

Reaction Steps

Sodium hydride (239 mg, 6.0 mmol) and a drop of methanol were added to a solution (10 ml) of methyl 3-[2-(3,4-diethoxyphenyl)thiazole-4-yl]propionate (1.0 g, 3.0 mmol) and methyl 3-ethoxypyridine-2-carboxylate (702 mg, 3.9 mmol) in dimethoxyethane, followed by heating under reflux for 2 hours. After cooling to room temperature, a saturated aqueous ammonium chloride solution was added to the reaction mixture, and the resulting mixture was subjected to extraction with ethyl acetate. The organic layer was washed with a saturated salt solution, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=2/3). The solvent was distilled off under reduced pressure, to thereby obtain 740 mg (yield: 51%) of methyl 2-[2-(3,4-diethoxyphenyl)thiazole-4-ylmethyl]-3-(3-ethoxypyridine-2-yl)-3-oxopropionate as a yellow oil.

Provenance & Evidence