Hydrochloric Acid → Methyl 5-(2-hydroxyethyl)pyrazine-2-carboxylate

Participants

Reaction Steps

To a solution of methyl 5-(2-oxoethyl)pyrazine-2-carboxylate (5.08 g) in methanol (50 mL) was added sodium borohydride (1.07 g) under ice-cooling, followed by stirring at the same temperature for 60 minutes. To the reaction mixture was added 1 M hydrochloric acid under ice-cooling to adjust the pH to 3. Saturated brine was added thereto, followed by extraction with a solvent (ethyl acetate:isopropyl alcohol=4:1). The organic layer was dried over anhydrous magnesium sulfate and concentrated. The obtained crude product was purified by silica gel column chromatography (hexane:ethyl acetate=4:1-0:1, chloroform:methanol=1:0-30:1) to obtain methyl 5-(2-hydroxyethyl)pyrazine-2-carboxylate (1.34 g) as a red-brown oily substance.

Provenance & Evidence