Sodium Methoxide → (2-Methoxy-6-methylpyridin-4-yl)methanol

Temperature

80 °C

Sodium methoxide (11.3 mL, 28% solution in methanol) was added to a solution of (2-chloro-6-methylpyridin-4-yl)methanol (1.75 g) in DMF (18 mL), and the mixture was stirred at 80° C. for 12 hours. Subsequently, the reaction mixture was stirred at 120° C. for seven hours. The reaction mixture was concentrated under reduced pressure, and a saturated aqueous ammonium chloride solution was added to the residue, followed by extraction with ethyl acetate. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 10% to 70%) to give the title compound (1.1 g).

1. stirringSubsequently, the reaction mixture was stirred at 120° C. for seven hours
2. concentrationThe reaction mixture was concentrated under reduced pressure
3. additiona saturated aqueous ammonium chloride solution was added to the residue
4. extractionfollowed by extraction with ethyl acetate
5. concentrationThe organic layer was concentrated under reduced pressure
6. customthe residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 10% to 70%)

ORD record

ord-694d2e280bf9438d967e837a11970c19

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08563565B2