Hydrochloric Acid → 2-Tert-butyl-1,3-thiazole-4-carboxylic acid

HRID 2390539Notes

Reaction equation

HRID 2390539 reaction equation
[OH-].[Li+].[C:3]([C:7]1[S:8][CH:9]=[C:10]([C:12]([O:14]CC)=[O:13])[N:11]=1)([CH3:6])([CH3:5])[CH3:4].Cl>C1COCC1.O>[C:3]([C:7]1[S:8][CH:9]=[C:10]([C:12]([OH:14])=[O:13])[N:11]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58790291Ethyl 2-(tert-butyl)thiazole-4-carboxylate

Product 1

HCID 288755552-Tert-butyl-1,3-thiazole-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (2.8 g, 120.25 mmol) was added to a stirred mixture of ethyl 2-tert-butylthiazole-4-carboxylate (6.56 g, 30.76 mmol) in THF (100 mL) and water (40 mL). After 16 h, HCl (62.5 mL, 125 mmol) was added and the solution concentrated to ˜40 mL. The reaction mixture was partitioned between EtOAc and brine. The aqueous layer was extracted with EtOAc (×3). The combined organic layers were dried over magnesium sulphate, filtered and evaporated in vacuo to give the sub-title compound as an off white/yellow solid. Yield: 5.41 g

Workup

  1. concentrationthe solution concentrated to ˜40 mL
  2. customThe reaction mixture was partitioned between EtOAc and brine
  3. extractionThe aqueous layer was extracted with EtOAc (×3)
  4. dry with materialThe combined organic layers were dried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-4974d9ee68cb4f87a55ab8def3fc79d8
Source dataset
uspto-grants-2012_09
Patent number
US08273774B2

Reaction notes

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