Hydrochloric Acid → 6-Methoxy-5-neopentylpyridin-3-ol

Under an argon atmosphere, to a solution of 5-bromo-2-methoxy-3-neopentylpyridine (4.38 g) in THF (40 mL) was added a 1.6 M solution of n-butyllithium in hexane (12.7 mL) at −78° C., and the mixture was stirred for 5 min. Trimethoxyborane (2.31 mL) was added at −78° C., and the mixture was stirred at room temperature for 14 hr. 8N Aqueous sodium hydroxide solution (2.54 mL) and 38% aqueous hydrogen peroxide (5.20 mL) were added to the reaction mixture at 0° C., and the mixture was stirred at room temperature for 5 hr. To the reaction mixture was added saturated aqueous sodium thiosulfate solution at 0° C., and the mixture was neutralized with 2N hydrochloric acid (23.4 mL). The reaction mixture was extracted with ethyl acetate, and the extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.56 g) as a white solid.

1. stirringthe mixture was stirred at room temperature for 14 hr
2. stirringthe mixture was stirred at room temperature for 5 hr
3. extractionThe reaction mixture was extracted with ethyl acetate
4. washthe extract was washed with water and saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. customThe solvent was evaporated under reduced pressure
7. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

ORD record

ord-c654eb1113a54b0c9f8c7b571c1a9832

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09382188B2