Hydrochloric Acid → 5-Cyclopropyl-1,2-oxazole-3-carboxylic acid

HRID 58532

Reaction equation

HRID 58532 reaction equation
[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]([O:11]CC)=[O:10])[CH:5]=2)[CH2:3][CH2:2]1.[OH-].[Na+].Cl>>[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]([OH:11])=[O:10])[CH:5]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 55251041Ethyl 5-cyclopropylisoxazole-3-carboxylate

Product 1

HCID 10921135-Cyclopropyl-1,2-oxazole-3-carboxylic acidYield 96%

Procedure

The mixture of ethyl 5-cyclopropylisoxazole-3-carboxylate (0.550 g; 3.04 mmol) and 1M aqueous sodium hydroxide (9.11 mL; 9.11 mmol) was stirred at room temperature during the weekend (72 h). The pH of the solution was adjusted to 1 by addition of 6N hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was dried over magnesium sulfate and was evaporated to furnish 0.446 g (96%) of 5-cyclopropylisoxazole-3-carboxylic acid as a solid.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe ethyl acetate layer was dried over magnesium sulfate
  3. customwas evaporated

Sources & evidence

ORD record
ord-9de27717436c4b158c7844f65c9c1883
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Linked notes

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