Lithium Hydroxide → 2-Ethyl-1,3-thiazole-4-carboxylic acid

HRID 2390545Notes

Reaction equation

HRID 2390545 reaction equation
[OH-].[Li+].[CH2:3]([C:5]1[S:6][CH:7]=[C:8]([C:10]([O:12]CC)=[O:11])[N:9]=1)[CH3:4]>O.C1COCC1>[CH2:3]([C:5]1[S:6][CH:7]=[C:8]([C:10]([OH:12])=[O:11])[N:9]=1)[CH3:4]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 15056276Ethyl 2-ethyl-1,3-thiazole-4-carboxylate

Product 1

HCID 252188552-Ethyl-1,3-thiazole-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (1.405 g, 58.68 mmol) in water (13.75 mL) was sonicated for 10 min before being added to a stirred mixture of ethyl 2-ethylthiazole-4-carboxylate (2.78 g, 15.01 mmol) in THF (55 mL). The reaction was stirred art RT overnight. The solution was diluted with water and extracted with EtOAc (×3). The organic extracts were discarded. The aqueous was acidified with 2M HCl and extracted with EtOAc (×3). The combined organic layers were washed with brine, dried over magnesium sulphate, filtered and evaporated in vacuo to give the sub-title compound as a brown oil which solidified on standing to give a waxy solid. Yield: 1.02 g

Workup

  1. extractionextracted with EtOAc (×3)
  2. extractionextracted with EtOAc (×3)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-67b98337be344700ad282feff3ca83bc
Source dataset
uspto-grants-2012_09
Patent number
US08273774B2

Reaction notes

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