Sodium Hydroxide → 5-Oxazol-4-yl-thiophene-3-carboxylic acid

HRID 2068664Notes

Reaction equation

HRID 2068664 reaction equation
C[O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10]2[N:11]=[CH:12][O:13][CH:14]=2)[S:7][CH:6]=1)=[O:4].[OH-].[Na+]>CO>[O:13]1[CH:14]=[C:10]([C:8]2[S:7][CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:9]=2)[N:11]=[CH:12]1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 581102445-Oxazol-4-yl-thiophene-3-carboxylic acid methyl ester

Product 1

HCID 581102215-Oxazol-4-yl-thiophene-3-carboxylic acidYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Oxazol-4-yl-thiophene-3-carboxylic acid methyl ester (0.338 g, 1.62 mmol) was dissolved in methanol (3 mL) and sodium hydroxide (1 N, 2.1 mL) was added. The mixture was stirred at room temperature for 2 hours then a further amount of sodium hydroxide (1 N, 1 mL) was added and stirring continued overnight. The mixture was concentrated and the residue treated with HCl (1 N, 3.5 mL). The resultant precipitate was collected by filtration to give the title compound as a tan/off-white solid (0.158 g). The filtrate was passed through an SCX-2 cartridge (20 g) and concentrated to give a further amount of the title compound as a tan solid (0.078 g). LCMS m/z 196.13 [M+H]+ R. T.=3.22 min (Analytical Method 9).

Workup

  1. stirringstirring continued overnight
  2. concentrationThe mixture was concentrated
  3. additionthe residue treated with HCl (1 N, 3.5 mL)
  4. filtrationThe resultant precipitate was collected by filtration

Sources & evidence

ORD record
ord-f502ff8750ca488aa0aebeac9f6aec7f
Source dataset
uspto-grants-2012_10
Patent number
US08299063B2

Reaction notes

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