Methyl iodide → 5-Methoxy-2-methylpyridine

5-Hydroxy-2-methylpyridine (16.4 g, 150.3 mmol) was added to a suspension of KOH (34.6 g, 616 mmol) in DMSO (250 ml) and stirred for 1 h at r.t. followed by the dropwise addition of methyl iodide (10.3 ml, 165 mmol). The reaction mixture was stirred for a further 16 h, poored onto ice-cold water (500 ml) and extracted with diethyl ether (4×350 ml). The combined ether extracts were washed with water (50 ml), brine (50 ml) and dried (MgSO4). Filtration and concentration of the filtrate under reduced pressure gave a crude oil which was purified over silica gel (ethyl acetate/n-heptane 1:2 to 1:1): light brown oil 10.5 g (54%);

1. stirringThe reaction mixture was stirred for a further 16 h, poored onto ice-cold water (500 ml)
2. extractionextracted with diethyl ether (4×350 ml)
3. washThe combined ether extracts were washed with water (50 ml), brine (50 ml)
4. dry with materialdried (MgSO4)
5. filtrationFiltration and concentration of the filtrate under reduced pressure
6. customgave a crude oil which
7. customwas purified over silica gel (ethyl acetate/n-heptane 1:2 to 1:1)

ORD record

ord-f96f7d03295a4fc99c02e483ebb990c4

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07253158B2