Sodium Hydroxide → HCID 12487457, compound

A 2 N aqueous sodium hydroxide solution (10 mL) and water (20 mL) were added to 4-(chloromethyl)pyridine hydrochloride (1.6 g, 10 mmol), and the reaction mixture was extracted with chloroform (20 mL) twice. The chloroform layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. m-Chloroperoxybenzoic acid (65%, 5.3 g, 20 mmol) was added to a solution of the resulting residue in dichloromethane (20 mL), and then the mixture was stirred at room temperature for 17 hours. Chloroform (100 mL) and a saturated aqueous sodium hydrogencarbonate solution (120 mL) were added to the reaction mixture, and then the chloroform layer was washed with a saturated aqueous sodium hydrogencarbonate solution (80 ml) and brine (100 mL). The chloroform layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 300 mg of the title reference compound as a brown solid. (Yield 21%)

1. extractionthe reaction mixture was extracted with chloroform (20 mL) twice
2. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
3. customthe solvent was evaporated under reduced pressure
4. washthe chloroform layer was washed with a saturated aqueous sodium hydrogencarbonate solution (80 ml) and brine (100 mL)
5. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
6. customthe solvent was evaporated under reduced pressure
7. customThe resulting residue was purified by silica gel column chromatography
8. customto give 300 mg of the title reference compound as a brown solid

ORD record

ord-b0cf9d0ec9ae472fb67ede87f81320e7

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08518973B2