Butyric Acid → methyl 4-acetyltetrahydro-2H-pyran-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

Add butanoic acid, 3-oxo-, methyl ester (18.60 mL, 172.20 mmol), bis(2-chloroethyl)ether (20.20 mL, 1.0 eq), potassium carbonate (52.42 g, 2.2 eq), and sodium iodide (25.88 g, 1.0 eq) in dimethylformamide (861 mL). Heat the reaction mixture at 80° C. overnight. Cool to room temperature. Add additional potassium carbonate (23.78 g) and sodium iodide (25.88 g). Heat the reaction mixture at 80° C. for two hours, then allow the mixture to cool to room temperature. Filter through Celite® and wash with ethyl acetate. Wash the filtrate with water and brine. Dry the organics over anhydrous sodium sulfate, filter, and concentrate in vacuo to give methyl 4-acetyltetrahydro-2H-pyran-4-carboxylate (23.06 g).

Provenance & Evidence