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

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).

1. additionwas added dropwise to the solution at 0° C.
2. filtrationThe mixture was filtered through Celite
3. extractionextracted with chloroform 3 times
4. customThe organic layer was separated
5. dry with materialdried over anhydrous sodium sulfate
6. customthe residue obtained
7. concentrationby concentrating the same under reduced pressure
8. customwas purified by silica gel column chromatography (n-hexane:ethyl acetate=90:10 to 65:35 to 50:50)

ORD record

ord-bb4b9471595f448b9dfd1a1fe0967f3b

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09302996B2