Hydrochloric Acid → (5-Chloropyrazin-2-yl)methanol

Participants

Reaction Steps

In tetrahydrofuran (75 mL) was dissolved methyl 5-chloropyrazin-2-carboxylate (2.589 g), 1M diisobutyl aluminum hydride-tetrahydrofuran solution (30 mL) was added dropwise to the solution at 0° C., and the mixture was stirred at the same temperature for 15 minutes. To the mixture were added water and 1N hydrochloric acid, then, a saturated aqueous sodium bicarbonate solution was added to the same to make the pH to 7. The mixture was filtered through Celite, and then, extracted with chloroform 3 times. The organic layer was separated, dried over anhydrous sodium sulfate, and the residue obtained by concentrating the same under reduced pressure was purified by silica gel column chromatography (n-hexane:ethyl acetate=90:10 to 65:35 to 50:50) to obtain (5-chloropyrazin-2-yl)methanol (465 mg).

Provenance & Evidence