Sulfuric Acid → 3-Ethyl 3,5-isoxazoledicarboxylate

HRID 58530

Reaction equation

HRID 58530 reaction equation
OS(O)(=O)=O.[OH:6][CH2:7][C:8]1[O:12][N:11]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:9]=1.CC([OH:21])C.C(OCC)(=O)C>O.CC(C)=O.[Cl-].[Na+].O.[O-2].[Cr+6].[O-2].[O-2]>[CH2:16]([O:15][C:13]([C:10]1[CH:9]=[C:8]([C:7]([OH:21])=[O:6])[O:12][N:11]=1)=[O:14])[CH3:17]

Participants

9

Reactant 4

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 8857Ethyl AcetateHCID 8027233Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate

Product 1

HCID 216484863-Ethyl 3,5-isoxazoledicarboxylateYield 70%

Reagents, catalysts & solvents 4

HCID 10219390chromium (VI) trioxideCatalystHCID 180AcetoneSolventHCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A 2M solution of the Jone's reagent was prepared by addition of 6 g of chromium (VI) oxide to a solution of H2SO4 (8.1 g) in water (25.5 mL). To a solution of ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate (4.00 g; 23.37 mmol) in acetone in an ice bath was added dropwise during a period of 20 min the Jone's reagent (27.71 mL; 51.42 mmol). The reaction mixture was then stirred at room temperature for additional 3.5 hours. 5 mL of 2-propanol were added and the stirring continued for further 1 hour. The solution became green. Brine (60 mL) and ethyl acetate (150 mL) were added to the reaction mixture and after separation, the organic layer was washed with an aqueous solution of sodium bisulphite (15 g in 100 mL of H2O) and with brine (100 mL). The organic layer was dried over magnesium sulfate. The evaporation of the solution furnished 3.03 g (70%) of 3-(ethoxycarbonyl)isoxazole-5-carboxylic acid as a white solid.

Workup

  1. waitthe stirring continued for further 1 hour
  2. customafter separation
  3. washthe organic layer was washed with an aqueous solution of sodium bisulphite (15 g in 100 mL of H2O) and with brine (100 mL)
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customThe evaporation of the solution

Sources & evidence

ORD record
ord-c56278181277486b80a005166deef8df
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Linked notes

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