Methanol → 5-(2-Furyl)isoxazole-3-carboxylic acid

HRID 606279Notes

Reaction equation

HRID 606279 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)[O:8][N:7]=1)=[O:5])C.CO.[OH-].[Li+]>C1COCC1>[O:12]1[CH:13]=[CH:14][CH:15]=[C:11]1[C:9]1[O:8][N:7]=[C:6]([C:4]([OH:5])=[O:3])[CH:10]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 7127810Ethyl 5-(2-furyl)isoxazole-3-carboxylate

Product 1

HCID 10909825-(2-Furyl)isoxazole-3-carboxylic acidYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.14 g of 5-furan-2-yl-isoxazole-3-carboxylic acid ethyl ester was dissolved in 130 mL of THF 130 mL and 25 mL of methanol before the slow addition of 80 mL of aqueous 1N lithium hydroxide. Stirring for 15 hrs was followed by the removal of THF and methanol under reduced pressure. The residue was acidified with 1N HCl to produce a precipitate which was then filtered, washed with distilled water and dried to produce 3.22 g of 5-furan-2-yl-isoxazole-3-carboxylic acid as a white solid (Yield: 90%).

Workup

  1. customwas followed by the removal of THF and methanol under reduced pressure
  2. customto produce a precipitate which
  3. filtrationwas then filtered
  4. washwashed with distilled water
  5. customdried

Sources & evidence

ORD record
ord-260f90099e4e4cabb744ef990103eba4
Source dataset
uspto-grants-2011_03
Patent number
US07915297B2

Reaction notes

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