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

HRID 1689381Notes

Reaction equation

HRID 1689381 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-f0d8f947cf6542d281cdd989cbb903db
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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