Methyl cyanoacetate → Methyl 4-cyanooxane-4-carboxylate

Participants

Reaction Steps

Methyl cyanoacetate (2.50 mL, 28.3 mmol) and 2-bromoethyl ether (4.63 mL, 36.8 mol) were dissolved in acetone (50 ml). To this, potassium carbonate (9.78 g, 70.8 mmol) was added and the mixture was heated to reflux for 8 hours. The reaction mixture was filtered and the mother liquid was concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/3) to give methyl 4-cyanotetrahydro-2H-pyran-4-carboxylate (2.93 g, yield: 61%).

Provenance & Evidence