Citric Acid → 1516805-43-8

Participants

Reaction Steps

A lanthanum(III) chloride-bis(lithium chloride) complex (0.6 M solution in THF, 16.7 mL, 10 mmol) was added to a solution of 1-(6-bromopyridin-3-yl)ethanone (2 g, 10 mmol) in THF (10 mL), and the mixture was stirred at room temperature for 1 hour. Methyl magnesium bromide (1.12 M solution in THF, 10.7 mL, 12 mmol) was added thereto at 0° C., and the mixture was stirred for 1 hour. A 10% citric acid aqueous solution was added to the reaction solution, and the solvent was distilled off under reduced pressure. The residue was diluted with ethyl acetate, and insoluble matter was filtered off through Celite. After extraction with ethyl acetate twice, combined organic layers were washed with brine and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. An internal salt of (methoxycarbonylsulfamoyl)triethylammonium hydroxide (2.86 g, 12 mmol) was added to a solution of the obtained residue in THF (20 mL), and the mixture was stirred at 60° C. for 2 hours. The solvent in the reaction solution was distilled off under reduced pressure, and ethyl acetate was added to the residue. The organic layer was washed with brine and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography [elute: hexane/ethyl acetate=98/2-80/20 (gradient)] to obtain the title compound (1.00 g, yield: 51%).

Provenance & Evidence