Sodium Methoxide → 2-Methoxy-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-3-nitro-pyridine
Reaction equation
[CH3:1][O-:2].[Na+].Cl[C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([CH3:14])=[C:7]([C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][C:16]=2[O:26][CH3:27])[N:6]=1>CO>[CH3:1][O:2][C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([CH3:14])=[C:7]([C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][C:16]=2[O:26][CH3:27])[N:6]=1Participants
4
Procedure
A solution of sodium methoxide in MeOH (14 ml, 25%, 60.7 mmol) is added to a solution of 2-chloro-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-3-nitro-pyridine (20 g, 55.14 mmol) in MeOH (170 ml) at room temperature. The mixture is refluxed for 8 hours. Additional sodium methoxide in MeOH (14 ml, 25%, 60.7 mmol) is added and refluxed for 15 hours. After cooling to room temperature, the mixture is concentrated under reduced pressure. Water (300 ml) is added to the concentrated mixture and the mixture is extracted with EtOAc. The combined extracts are washed with brine and dried over Na2SO4. The solvent is removed under reduced pressure and the residue is purified by flash column chromatography (hexane/EtOAc 20:1) to give 2-methoxy-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-3-nitro-pyridine as white solid. Rf (hexane/EtOAc=9:1)=0.32.