Lithium Hydroxide → HCID 22318576, compound

HRID 394787Notes

Reaction equation

HRID 394787 reaction equation
[OH-].[Li+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]([C:16]([O:18]C)=[O:17])=[CH:14][C:13]([S:20]([CH3:23])(=[O:22])=[O:21])=[N:12]2)=[CH:7][CH:6]=1>CO>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:15]([C:16]([OH:18])=[O:17])=[CH:14][C:13]([S:20]([CH3:23])(=[O:22])=[O:21])=[N:12]2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 18177321HCID 18177321, compound

Product 1

HCID 22318576HCID 22318576, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of lithium hydroxide (1.3 mL, 1.0 M, 1.3 mmol) was added to a suspension of methyl 1-(4-methoxyphenyl)-3-methylsulfonyl-pyrazole-5-carboxylate (272 mg, 0.88 mmol) in MeOH (10 mL) and stirred at room temperature 17 hours. The resulting mixture was concentrated and partitioned between EtOAc and H2O. The organic extracted was removed, and the aqueous extract was acidified with 1M HCl and extracted twice with EtOAc. The organic extracts from this extraction were combined, dried over Na2SO4, filtered, and evaporated to yield product (266 mg). 1H NMR (CDCl3+few drops MeOD) δ 7.45 (s, 1H), 7.38 (d, 2H, J=9.2), 6.96 (d, 2H, J=9.2), 3.86 (s, 3H), 3.25 (s, 3H).

Workup

  1. concentrationThe resulting mixture was concentrated
  2. custompartitioned between EtOAc and H2O
  3. extractionThe organic extracted
  4. customwas removed
  5. extractionthe aqueous extract
  6. extractionextracted twice with EtOAc
  7. extractionThe organic extracts from this extraction
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-468b5cc8cdd84d458ac46359fce4874d
Source dataset
uspto-grants-2003_08
Patent number
US06602895B2

Reaction notes

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