Sodium Hydroxide → 5-(2,5-Difluorobenzyl)isoxazole-3-carboxylic acid

HRID 58572Notes

Reaction equation

HRID 58572 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:5]=1[CH2:6][C:7]1[O:11][N:10]=[C:9]([C:12]([O:14]CC)=[O:13])[CH:8]=1>C(O)C>[F:3][C:4]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:5]=1[CH2:6][C:7]1[O:11][N:10]=[C:9]([C:12]([OH:14])=[O:13])[CH:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66831915Ethyl 5-(2,5-difluorobenzyl)isoxazole-3-carboxylate

Product 1

HCID 668320395-(2,5-Difluorobenzyl)isoxazole-3-carboxylic acidYield 84.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of sodium hydroxide 1M (28 mL; 28 mmol) was added to a solution of ethyl 5-(2,5-difluorobenzyl)isoxazole-3-carboxylate (2.50 g; 9.36 mmol) in ethanol (3 mL). The mixture was stirred at room temperature. After 1 hour, a precipitation occurred and the reaction mixture was allowed to stir for 30 minutes. The solution was acidified to pH 1 by addition of a solution of hydrochloric acid 6N. The precipitate was collected by filtration and dried under reduced pressure to give 1.90 g (84%) of 5-(2,5-difluorobenzyl)isoxazole-3-carboxylic acid as a white solid.

Workup

  1. customa precipitation
  2. stirringto stir for 30 minutes
  3. additionThe solution was acidified to pH 1 by addition of a solution of hydrochloric acid 6N
  4. filtrationThe precipitate was collected by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-c401efa968ba4ee0aae72eee21bb3643
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Reaction notes

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