Hydrochloric Acid → 3-Cyclopropyl-1,2-oxazole-4-carboxylic acid

HRID 2273573Notes

Reaction equation

HRID 2273573 reaction equation
C([O:3][C:4]([C:6]1[C:7]([CH:11]2[CH2:13][CH2:12]2)=[N:8][O:9][CH:10]=1)=[O:5])C.[OH-].[K+].Cl>C(O)C.O.O>[CH:11]1([C:7]2[C:6]([C:4]([OH:5])=[O:3])=[CH:10][O:9][N:8]=2)[CH2:12][CH2:13]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 57424032HCID 57424032, compound

Product 1

HCID 450847723-Cyclopropyl-1,2-oxazole-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 19096565Water ethanolSolvent

Procedure

5.6 g (31 mmol) of 3-Cyclopropyl-isoxazole-4-carboxylic acid ethyl ester were slowly added to a solution of 6.1 g (93 mmol, 85% purity) of potassium hydroxide in ethanol/water (1:3, 100 ml) at 0° C. The reaction mixture was stirred at room temperature for 16 h, diluted with water, acidified (pH=2) with 20% aqueous HCl and extracted with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered and the solvent was removed to yield 4.7 g (94%, 95% purity) of the title compound which did not need further purification.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. customthe solvent was removed

Sources & evidence

ORD record
ord-53b075df594b4885bcb304873d7abb92
Source dataset
uspto-grants-2015_09
Patent number
US09125414B2

Reaction notes

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