Lithium Hydroxide → 2-(1,1-Dimethylethyl)-5-thiazolecarboxylic acid

HRID 1930439Notes

Reaction equation

HRID 1930439 reaction equation
[C:1]([C:5]1[S:6][C:7]([C:10]([O:12]CC)=[O:11])=[CH:8][N:9]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>C1COCC1.O>[C:1]([C:5]1[S:6][C:7]([C:10]([OH:12])=[O:11])=[CH:8][N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58790083HCID 58790083, compound

Product 1

HCID 198855292-(1,1-Dimethylethyl)-5-thiazolecarboxylic acidYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-tert-butylthiazole-5-carboxylate (1.16 g, 5.44 mmol) in THF (10 mL) was added lithium hydroxide (0.45 g, 10.9 mmol) in water (5 mL) and the mixture was stirred for 16 h at RT. Solvents were removed under vacuum, and the thick liquid was diluted with water (5 mL) and acidified with 2M HCl solution to pH 4 to 5. The product precipitated, was filtered, washed with water (2×5 mL) and dried to provide 2-tert-butylthiazole-5-carboxylic acid as white solid (0.55 g, 55% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.32 (s, 1H), 1.39 (s, 9H); MS (ESI) m/z: 186.0 (M+H+).

Workup

  1. customSolvents were removed under vacuum
  2. additionthe thick liquid was diluted with water (5 mL)
  3. customThe product precipitated
  4. filtrationwas filtered
  5. washwashed with water (2×5 mL)
  6. customdried

Sources & evidence

ORD record
ord-c3d2962da3ed4ee49ef17b7108e699b6
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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