Hydrochloric Acid → 2-(Pentan-3-yl)thiazole-4-carboxylic acid

HRID 471152

Reaction equation

HRID 471152 reaction equation
O.[OH-].[Li+].[CH3:4][CH2:5][CH:6]([C:9]1[S:10][CH:11]=[C:12]([C:14]([O:16]CC)=[O:15])[N:13]=1)[CH2:7][CH3:8].Cl>C1COCC1.O>[CH3:4][CH2:5][CH:6]([C:9]1[S:10][CH:11]=[C:12]([C:14]([OH:16])=[O:15])[N:13]=1)[CH2:7][CH3:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 57989261Ethyl 2-(pentan-3-yl)thiazole-4-carboxylate

Product 1

HCID 579605932-(Pentan-3-yl)thiazole-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (2.07 g) was added to a solution of ethyl 2-(pentan-3-yl)thiazole-4-carboxylate (example 71, step c) (2.8 g) in a mixture of THF (80 mL) and water (20 mL). The resulting mixture was stirred overnight. The reaction was acidified with concentrated hydrochloric acid (6 mL) and the volatiles evaporated. The resulting aqueous mixture was saturated with sodium chloride and extracted with ethyl acetate (3×100 mL). The combined organic solutions were dried over sodium sulphate, filtered and evaporated to give the subtitled compound as a white solid. Yield 2.3 g

Workup

  1. customthe volatiles evaporated
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. dry with materialThe combined organic solutions were dried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-3e0db00481fa446ea4943f83014d7eb2
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Linked notes

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