Hydrochloric Acid → 5-(2-Benzyloxyethoxy)pyrazine-2-carboxylic acid

Participants

Reaction Steps

To a solution of 2-(benzyloxy)ethanol (1.94 g) in DMF (60 mL) was added 60% sodium hydride (510 mg) under ice-cooling, followed by stirring at room temperature for 30 minutes, and methyl 5-chloropyrazine-2-carboxylate (2 g) was added thereto in one portion in an ice bath, followed by stirring at room temperature for 15 minutes. To the reaction mixture was added 1 M hydrochloric acid in an ice bath, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1-1:1) to obtain a colorless oily substance. To a solution of the obtained colorless oily substance in methanol (50 mL) was added 1 M aqueous sodium hydroxide solution (15 mL) at room temperature, followed by stirring at room temperature for 2 hours. 1 M Hydrochloric acid was added to reaction mixture to adjust the pH to 2 under ice-cooling, followed by addition of water (about 200 mL). The resulting precipitate was collected by filtration while washing with a solvent (water:methanol=5:1), to obtain 5-[2-(benzyloxy)ethoxy]pyrazine-2-carboxylic acid (1.089 g) as a white solid.

Provenance & Evidence