Hydrochloric Acid → 4-(3-Phenyl-1,2,4-oxadiazol-5-yl)butanoic acid

Reaction equation

[C:1]1([C:7]2[N:11]=[C:10]([CH:12](C)[CH2:13][C:14](OC)=O)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:19].[Na+].Cl.[CH3:22][OH:23]>>[C:1]1([C:7]2[N:11]=[C:10]([CH2:12][CH2:13][CH2:14][C:22]([OH:23])=[O:19])[O:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 887Methanol

HCID 14798Sodium Hydroxide

HCID 66725791Methyl 3-(3-phenyl-1,2,4-oxadiazol-5-yl)butanoate

Product 1

HCID 6672524-(3-Phenyl-1,2,4-oxadiazol-5-yl)butanoic acidYield 99%

Procedure

To a solution of methyl 3-(3-phenyl-1,2,4-oxadiazol-5-yl)butanoate (1.53 g, 6.21 mmole) in methanol (10 ml) was added 1N NaOH (10 mL). After stirring at room temperature for 2 hours, the reaction solution was acidified to pH=3-4 with 6N HCl under an ice bath and then extracted with ethyl acetate three times. The combined organic layers were washed with water and then brine, dried over Na2SO4, filtered and concentrated to give the desired product (1.44 g, 99% yield) as white solid. LCMS calculated for C12H13N2O3 (M+H): 233.1; found: 233.1.