Sodium Hydroxide → 6-Chloro-2-methyl-3-(1H-1,2,3-triazol-4-yl)pyridine
Reaction equation
C(OC[N:9]1[CH:13]=[C:12]([C:14]2[C:15]([CH3:21])=[N:16][C:17]([Cl:20])=[CH:18][CH:19]=2)[N:11]=[N:10]1)(=O)C(C)(C)C.[OH-].[Na+]>CO>[Cl:20][C:17]1[N:16]=[C:15]([CH3:21])[C:14]([C:12]2[N:11]=[N:10][NH:9][CH:13]=2)=[CH:19][CH:18]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
[4-(6-Chloro-2-methylpyridin-3-yl)-1H-1,2,3-triazol-1-yl]methyl pivalate (350 mg, 0.96 mmol) was taken up in methanol (3.9 ml) at room temperature. Aqueous sodium hydroxide (1.0M, 4.8 ml, 4.8 mmol) was added, and the mixture was allowed to react for 2 hours. The reaction was then extracted three times with diethyl ether. The combined organic fractions were washed with water. The combined aqueous layers were adjusted to pH 7.0 via dropwise addition of 6 M aqueous hydrochloric acid. The neutralized mixture was saturated with solid sodium chloride and extracted three times with ethyl acetate. All the organic layers were combined, dried over anhydrous magnesium sulfate, filtered, and concentrated to afford the title compound.