Lithium hydroxide, monohydrate → HCID 68327934, compound

HRID 2281241Notes

Reaction equation

HRID 2281241 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:13]([CH3:20])([CH3:19])[C:14]([O:16]CC)=[O:15])[S:11][CH:12]=2)=[CH:4][CH:3]=1.O.[OH-].[Li+]>C1COCC1.C(O)C.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([C:13]([CH3:20])([CH3:19])[C:14]([OH:16])=[O:15])[S:11][CH:12]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68327803HCID 68327803, compound

Product 1

HCID 68327934HCID 68327934, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

To a stirred solution of ethyl 2-(4-(4-fluorophenyl)thiazol-2-yl)-2-methylpropanoate (0.900 g, 3.07 mmol) in 1:1:1 THF/ethanol/water (15 mL) was added lithium hydroxide monohydrate (0.451 g, 10.7 mmol). After overnight stirring, the reaction was concentrated and redissolved in water (80 mL). The solution was washed with ether (1×50 mL), acidified with the addition of 1 N HCl (15 mL) and extracted with ethyl acetate (2×50 mL). The combined extracts were dried (Na2SO4) and concentrated to afford 2-(4-(4-fluorophenyl)thiazol-2-yl)-2-methylpropanoic acid as a pale golden solid (0.808 g, 99%).

Workup

  1. concentrationthe reaction was concentrated
  2. dissolutionredissolved in water (80 mL)
  3. washThe solution was washed with ether (1×50 mL)
  4. additionacidified with the addition of 1 N HCl (15 mL)
  5. extractionextracted with ethyl acetate (2×50 mL)
  6. dry with materialThe combined extracts were dried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-847e0106b3f9435eb776a5312654fb4e
Source dataset
uspto-grants-2015_09
Patent number
US09139580B2

Reaction notes

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