Lithium Hydroxide → 5-(2-Furyl)isoxazole-3-carboxylic acid

HRID 1896689Notes

Reaction equation

HRID 1896689 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.[OH-].[Li+]>C1COCC1.CO>[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 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-furan-2-yl-isoxazole-3-carboxylic acid ethyl ester (4.14 g) in THF (130 mL) and methanol (25 mL) was slowly added 1N lithium hydroxide aqueous solution (80 mL). The resulting mixture was stirred for 15 hours, and then concentrated under reduced pressure. The remaining solution was acidified with 1N hydrochloric acid to form a solid, and the solid was filtered, washed with distilled water, dried to give 3.22 g of 5-furan-2-yl-isoxazole-3-carboxylic acid (yield: 90%) as a white solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto form a solid
  3. filtrationthe solid was filtered
  4. washwashed with distilled water
  5. customdried

Sources & evidence

ORD record
ord-5f015aed813540e08b758222af6fb3dd
Source dataset
uspto-grants-2013_08
Patent number
US08518978B2

Reaction notes

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