Sodium Hydroxide → (5-Chloropyrazin-2-yl)methanol

Participants

Reaction Conditions

Reaction Steps

Diisobutylaluminum hydride (4.29 mL, 4.29 mmol) was added dropwise over 5 min to a solution of methyl 5-chloropyrazine-2-carboxylate (185 mg, 1.07 mmol) in tetrahydrofuran (10 mL) at −70° C. under an atmosphere of nitrogen. The reaction mixture was stirred at −70° C. for 5 min and then allowed to reach ambient temperature and stirred over night. The reaction mixture was cooled on ice and approximately 2 mL of 1 M sodium hydroxide was added dropwise while stirring. The reaction mixture was diluted with diethyl ether and stirred for 45 min at ambient temperature and then filtered. The filtrate was concentrated in vacuo and the residue was purified by column chromatography using a gradient of ethyl acetate in heptane to yield 43 mg (28%) of the title product; 1H NMR (400 MHz, DMSO-d6) δ ppm 8.72 (d, 1 H), 8.52-8.55 (m, 1 H), 5.71 (t, 1 H), 4.64 (d, 2 H);

Provenance & Evidence