Sodium Hydroxide → 5-(3-Fluorobenzyl)isoxazole-3-carboxylic acid

HRID 1918515Notes

Reaction equation

HRID 1918515 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[CH2:5][C:6]1[O:10][N:9]=[C:8]([C:11]([O:13]CC)=[O:12])[CH:7]=1.[OH-].[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[CH2:5][C:6]1[O:10][N:9]=[C:8]([C:11]([OH:13])=[O:12])[CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66831768Ethyl 5-(3-fluorobenzyl)isoxazole-3-carboxylate

Product 1

HCID 668321075-(3-Fluorobenzyl)isoxazole-3-carboxylic acidYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethanol (3 mL) was added to the mixture of ethyl 5-(3-fluorobenzyl)isoxazole-3-carboxylate (0.688 g; 2.82 mmol) and 1M sodium hydroxide (10.5 mL; 10.5 mmol). The mixture was stirred overnight at room temperature and was concentrated under reduced pressure to remove ethanol. The aqueous solution was acidified by addition of 6N hydrochloric acid to pH 0-1. The formed precipitate was collected by filtration and was dried. 0.5026 g (82%) of 5-(3-fluorobenzyl)isoxazole-3-carboxylic acid was obtained as a white solid which was directly used in the next step.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customto remove ethanol
  3. additionThe aqueous solution was acidified by addition of 6N hydrochloric acid to pH 0-1
  4. filtrationThe formed precipitate was collected by filtration
  5. customwas dried

Sources & evidence

ORD record
ord-1cd63b5b526c41069f9520dfbd42e07b
Source dataset
uspto-grants-2013_12
Patent number
US08618138B2

Reaction notes

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