Potassium Carbonate → Methyl 4-((5-chloro-6-isobutoxypyridin-3-yloxy)methyl)-3-methoxybenzoate

Participants

Reaction Steps

To a solution of methyl 4-(bromomethyl)-3-methoxybenzoate (250 mg, 0.965 mmol) in acetone (20.0 mL) were added potassium carbonate (267 mg, 1.93 mmol) and 5-chloro-6-isobutoxypyridin-3-ol (Preparation 1, 195 mg, 0.965 mmol) and the reaction mixture was heated at reflux for 16 hours, then allowed to cool to room temperature. The solvent was removed in vacuo to yield a yellow solid, which was partitioned between EtOAc (30.0 mL) and water (50.0 mL). The aqueous was further extracted with EtOAc (2×30 mL). The combined organics were washed with sodium hydroxide solution (1 M, 30 mL) then brine (50 mL), dried over sodium sulfate and the solvent was removed in vacuo to yield the title compound as a pale yellow solid.

Provenance & Evidence