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

HRID 2368616Notes

Reaction equation

HRID 2368616 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

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 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.

Workup

  1. extractionextracted with ethyl acetate three times
  2. washThe combined organic layers were washed with water
  3. dry with materialbrine, dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a8117ef852d24070b3647937c659fcf4
Source dataset
uspto-grants-2014_04
Patent number
US08703783B2

Reaction notes

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