Lithium Hydroxide → 2-Cyclohexyl-1,3-thiazole-4-carboxylic acid

HRID 402182Notes

Reaction equation

HRID 402182 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[S:9][CH:10]=1)=[O:5])C.[Li+].[OH-]>O>[CH:11]1([C:8]2[S:9][CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=2)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57956421Ethyl 2-cyclohexylthiazole-4-carboxylate

Product 1

HCID 234049342-Cyclohexyl-1,3-thiazole-4-carboxylic acidYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-cyclohexylthiazole-4-carboxylic acid ethyl ester (116, 6.8 g, 28.5 mmol) in water was added 1M LiOH (50 mL). The solution was kept at room temperature and monitored by LC-MS. When the hydrolysis was completed the reaction mixture was neutralized with myriatic acid and extracted with ethyl acetate and diethyl ether. The organic phase was dried (Na2SO4), filtered and concentrated under reduced pressure to give 5.0 g (83%) of the title compound 117: m/z=212 (M+H)+.

Workup

  1. customwas kept at room temperature
  2. extractionextracted with ethyl acetate and diethyl ether
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-98ffb5f3389e43e1bc4eec0dab76d9f5
Source dataset
uspto-grants-2014_06
Patent number
US08741926B2

Reaction notes

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