Potassium Carbonate → Methyl 4-{[(5-chloro-6-isobutoxypyridin-3-yl)oxy]methyl}benzoate

Participants

Reaction Steps

To a solution of methyl 4-(bromomethyl)benzoate (250 mg, 1.09 mmol) in acetone (20 mL) were added potassium carbonate (302 mg, 2.18 mmol) and 5-chloro-6-isobutoxypyridin-3-ol (Preparation 1, 220 mg, 1.09 mmol) and the reaction heated at reflux overnight. The reaction was allowed to cool to room temperature, the solvent removed under reduced pressure and the resulting yellow solid dissolved in ethyl acetate (30 mL). The solution was transferred to a separating funnel containing water (50 mL), the organic layer separated and the aqueous extracted with ethyl acetate (2×30 mL). The combined organic extracts were washed with sodium hydroxide (1.0 M aqueous solution, 30 mL), then brine (50 mL), dried over sodium sulphate and filtered to give the title compound as pale yellow solid (369 mg, 97%).

Provenance & Evidence