Toluene → HCID 10419796, compound

Participants

Reaction Conditions

Reaction Steps

3-(1,3-Dioxolan-2-yl)-1-pyridinium iodide (1.85 g, 6.31 mmol) was dissolved in water (40 mL). To this, a solution of potassium ferricyanide (22.9 g, 69.4 mmol) in water (50 mL) was added dropwise under a nitrogen atmosphere at 0° C. over 1 hour. To this, a solution of potassium hydroxide (55.9 g, 100 mmol) in water (9.5 mL) was added dropwise at the same temperature over 30 minutes. To this, toluene (65 mL) was added and the mixture was stirred at 40° C. for 30 minutes. Then, extraction with dichloromethane was performed, followed by drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by column chromatography (hexane/ethyl acetate=1/1) to give a 73:27 mixture (933 mg, yield: 82%) of 1-methyl-5-(1,3-dioxolan-2-yl)-2(1H)-pyridone and 1-methyl-3-(1,3-dioxolan-2-yl)-2(1H)-pyridone.

Provenance & Evidence