Acetic Anhydride → (5-Bromo-4-isobutoxypyridin-2-yl)methanol

Temperature

80 °C

A mixture of 5-bromo-4-isobutoxy-2-methylpyridine 1-oxide (3.40 g) and acetic anhydride (50 mL) was stirred at 80° C. for 1 hr. The solvent in the reaction mixture was evaporated under reduced pressure, and the residue was dissolved in THF (50 mL) and methanol (25 mL). 1N Aqueous sodium hydroxide solution (50 mL) was added to the obtained solution, and the reaction mixture was stirred at room temperature for 15 min. 1N Hydrochloric acid (50 mL) was added to the reaction mixture at 0° C., and the mixture was extracted with ethyl acetate. 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 (2.20 g) as a pale-yellow oil.

1. customThe solvent in the reaction mixture was evaporated under reduced pressure
2. dissolutionthe residue was dissolved in THF (50 mL)
3. addition1N Aqueous sodium hydroxide solution (50 mL) was added to the obtained solution
4. stirringthe reaction mixture was stirred at room temperature for 15 min
5. addition1N Hydrochloric acid (50 mL) was added to the reaction mixture at 0° C.
6. extractionthe mixture was extracted with ethyl acetate
7. washThe extract was washed with water and saturated brine
8. dry with materialdried over anhydrous magnesium sulfate
9. customThe solvent was evaporated under reduced pressure
10. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

ORD record

ord-1e37d9607ec04fde8d9ec662c09e514b

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181186B2