Hydrochloric Acid → (2-Chloropyridin-4-yl)methanol

A 0.95 M solution of diisobutylaluminum hydride in hexane (200 mL, 190 mmol) was added dropwise to a solution of 2-chloroisonicotinic acid methyl ester (11 g, 62 mmol) in anhydrous tetrahydrofuran (300 mL) under a nitrogen atmosphere under ice-cooling, and then the mixture was stirred under ice-cooling for 2 hours. After that, 1 N hydrochloric acid (200 mL) was added thereto, the mixture was stirred at room temperature for 1 hour. A saturated aqueous sodium hydrogencarbonate solution (400 mL) was added to the reaction mixture, then the whole was extracted with ethyl acetate (100 mL) three times. The ethyl acetate layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure to give 8.5 g of the title reference compound as a white solid. (Yield 95%)

1. temperaturecooling
2. temperaturecooling for 2 hours
3. stirringthe mixture was stirred at room temperature for 1 hour
4. extractionthe whole was extracted with ethyl acetate (100 mL) three times
5. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
6. customthe solvent was evaporated under reduced pressure
7. customto give 8.5 g of the title reference compound as a white solid

ORD record

ord-93f74475f45f4e178fa3a0677b6af731

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08518973B2