Lithium Hydroxide → 2-Thiazolecarboxylic acid, 4-(1-methylethyl)-

HRID 471104Notes

Reaction equation

HRID 471104 reaction equation
[CH:1]([C:4]1[N:5]=[C:6]([C:9]([O:11]CC)=[O:10])[S:7][CH:8]=1)([CH3:3])[CH3:2].[OH-].[Li+]>CO.C1COCC1.O>[CH:1]([C:4]1[N:5]=[C:6]([C:9]([OH:11])=[O:10])[S:7][CH:8]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 10821861Ethyl 4-isopropylthiazole-2-carboxylate

Product 1

HCID 224993072-Thiazolecarboxylic acid, 4-(1-methylethyl)-

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

A solution of ethyl 4-isopropylthiazole-2-carboxylate (example 53, step a) (2.2 g) in a mixture of methanol (10 mL) and THF (20 mL) was treated with a solution of lithium hydroxide (0.264 g) in water (20 mL). The reaction mixture was stirred at 20° C. for 24 hours. The organic solvent was removed under reduced pressure and the remaining aqueous mixture was partitioned between ethyl acetate and water. The aqueous layer was acidified with 2M hydrochloric acid and extracted twice with ethyl acetate, the combined organics were washed with brine, dried over sodium sulphate, filtered and the solvent evaporated under reduced pressure. The crude product was triturated with cyclohexane to afford the subtitled compound. Yield 0.93 g.

Workup

  1. customThe organic solvent was removed under reduced pressure
  2. customthe remaining aqueous mixture was partitioned between ethyl acetate and water
  3. extractionextracted twice with ethyl acetate
  4. washthe combined organics were washed with brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customthe solvent evaporated under reduced pressure
  8. customThe crude product was triturated with cyclohexane

Sources & evidence

ORD record
ord-dbe70c69b87348afaec7547c0c4543db
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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