Lithium Hydroxide → 2-(Trifluoromethyl)-1,3-thiazole-4-carboxylic acid

HRID 872680

Reaction equation

HRID 872680 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[S:4][CH:5]=[C:6]([C:8]([O:10]CC)=[O:9])[N:7]=1.[OH-].[Li+]>C1COCC1.CO>[F:14][C:2]([F:1])([F:13])[C:3]1[S:4][CH:5]=[C:6]([C:8]([OH:10])=[O:9])[N:7]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 20079591Ethyl 2-(trifluoromethyl)-1,3-thiazole-4-carboxylate

Product 1

HCID 288755572-(Trifluoromethyl)-1,3-thiazole-4-carboxylic acidYield 93%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Ethyl 2-(trifluoromethyl)thiazole-4-carboxylate (400 mg, 1.176 mmol) was dissolved in THF/methanol mixture (9:1) and 1M lithium hydroxide (3.55 ml, 3.55 mmol) was added slowly. The reaction mixture was stirred at RT for 1 hour, pH was adjusted to 2 and the reaction mixture was extracted three times with ethyl acetate. Ethyl acetate phases were combined, dried and evaporated to dryness. Yield 93%. m/z [197.1+1]

Workup

  1. extractionthe reaction mixture was extracted three times with ethyl acetate
  2. customdried
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-3cb7e4741a9e40bfbd87db20081dc1ec
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Linked notes

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