Lithium Hydroxide → 5-Acetyl-1,2-oxazole-3-carboxylic acid

HRID 872697Notes

Reaction equation

HRID 872697 reaction equation
[C:1]([C:4]1[O:8][N:7]=[C:6]([C:9]([O:11]CC)=[O:10])[CH:5]=1)(=[O:3])[CH3:2].[OH-].[Li+]>C1COCC1.CO.O>[C:1]([C:4]1[O:8][N:7]=[C:6]([C:9]([OH:11])=[O:10])[CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 27363535-Acetyl-isoxazole-3-carboxylic acid ethyl ester

Product 1

HCID 178675215-Acetyl-1,2-oxazole-3-carboxylic acidYield 29.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Ethyl 5-acetylisoxazole-3-carboxylate (300 mg, 1.638 mmol) was dissolved in THF/methanol mixture (9:1) and 1M lithium hydroxide (3.28 ml, 3.28 mmol) was added slowly. The reaction mixture was stirred at RT for 40 min, diluted with water and pH was adjusted to 3. The reaction mixture was extracted three times with ethyl acetate. Ethyl acetate phases were combined, washed with brine, dried and evaporated to dryness to yield the title compound (29.9%). m/z [155.1+1].

Workup

  1. extractionThe reaction mixture was extracted three times with ethyl acetate
  2. washwashed with brine
  3. customdried
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-96171be4ce164dd9a89f93ee8e5e8507
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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