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

Participants

Reaction Steps

To a solution of methyl 5-formylpyrazine-2-carboxylate (2.47 g) in THF (20 mL) was added sodium borohydride (170 mg) portionwise over 10 mins. After stirring for 1 h, methanol (10 mL) was added. The reaction mixture was stirred for a further 20 mins, and then HCl (1 N, aq., 20 mL) and brine (20 mL) were added. The mixture was extracted with EtOAc (3×40 mL) and the combined organic portions dried over MgSO4 and evaporated to afford the title compound (1.31 g). 1H NMR (400 MHz, CDCl3) δ ppm 4.07 (s, 3 H), 4.98 (br. s., 2 H), 8.80 (s, 1 H), 9.27 (s, 1 H)

Provenance & Evidence