Lithium Hydroxide → HCID 22318576, compound

HRID 2186222Notes

Reaction equation

HRID 2186222 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): δ7.45 (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-e84fb15f914e4c9a940f3b0417607590
Source dataset
uspto-grants-2002_06
Patent number
US06403620B1

Reaction notes

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