Reaction #1747898

Reaction equation

2-hydroxy-4-methylpyridine

iodomethane

→

2-methoxy-4-methylpyridine

Yield 71.0%

Solvents

chloroform

Conditions

Workup

1. 1
   Filtrationfiltered through Celite
2. 2
   Washwashed with ether
3. 3
   ConcentrationThe filtrate was concentrated below 20° C.
4. 4
   Otherthe residue was purified by chromatography with pentane/ether (5:1)

Procedure

To a stirred solution of 2-hydroxy-4-methylpyridine (10 g, 92 mmol) in chloroform (350 mL) was added at room temperature silver carbonate (34.2 g, 124 mmol) and iodomethane (130 g, 920 mmol). The reaction mixture was stirred in the dark for 48 h, and then filtered through Celite and washed with ether. The filtrate was concentrated below 20° C., and the residue was purified by chromatography with pentane/ether (5:1) to afford 2-methoxy-4-methylpyridine as a colorless oil (8.0 g, 71%). 1H NMR (CDCl3) δ 8.02 (d, 1H, J=5.4 Hz), 6.69 (d, 1H, J=5.4 Hz), 6.55 (s, 1H), 3.91 (s, 3H), 2.28 (s, 3H); 13C NMR (CDCl3) δ 164.40, 149.72, 146.31, 118.21, 110.88, 53.17, 20.81. MS m/z (%): 123 (M+, 76), 122 (100).

Source