Hydrogen Peroxide → 6-(Cyclopropylmethoxy)pyridin-3-ol

Temperature

0 °C

To a solution of 5-bromo-2-(cyclopropylmethoxy)pyridine (1.88 g) in THF (15 mL) was added 1.6M n-butyllithium-hexane solution (7.25 mL) at −78° C., and the mixture was stirred at the same temperature for 20 min. Trimethylborane (1.29 mL) was added to this solution, and the mixture was stirred at −78° C. for 30 min. The reaction mixture was heated to 0° C., aqueous hydrogen peroxide (30%, 5 mL) and 8M aqueous sodium hydroxide solution (1.55 mL) were added thereto, and the mixture was stirred for 15 min. Water was added to the reaction mixture, the mixture was extracted twice with ethyl acetate, and the combined organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (855 mg).

1. stirringthe mixture was stirred at −78° C. for 30 min
2. stirringthe mixture was stirred for 15 min
3. extractionthe mixture was extracted twice with ethyl acetate
4. dry with materialthe combined organic layer was dried over anhydrous magnesium sulfate
5. customThe solvent was evaporated under reduced pressure
6. customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

ORD record

ord-c9cf9ddf13bd4a3eb8bfdb78ba40a378

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08703758B2