Lithium Hydroxide → HCID 18177264, compound

HRID 2186227Notes

Reaction equation

HRID 2186227 reaction equation
Br[CH:2](Br)[C:3]1[CH:7]=[C:6]([C:8]([O:10]CC)=[O:9])[N:5]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[N:4]=1.[OH-:22].[Li+]>C1COCC1.O>[CH:2]([C:3]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[N:5]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[N:4]=1)=[O:22]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 18177274HCID 18177274, compound

Product 1

HCID 18177264HCID 18177264, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 3-(dibromomethyl)-1-(4-methoxyphenyl)-1H-pyrazole-5-carboxylate (0.34 g, 0.813 mmol) was dissolved in 2 mL THF and lithium hydroxide (34 mg, 0.816 mmol) was dissolved in 0.5 mL water and added to the methanolic solution. After stirring at room temperature for 16 hours the solvent was evaporated, the residue was dissolved in 10 mL of water, acidified with 1N HCl and extracted with EtOAc to give 66 mg (33%) of the desired product after evaporation. 1H NMR (CDCl3): δ10.06 (s, 1H); 7.56 (s, 1H); 7.40 (d, J=9.1, 2H); 7.01 (d, J=9.1, 2H); 4.54 (s, 2H); 3.88 (s, 3H).

Workup

  1. additionadded to the methanolic solution
  2. customwas evaporated
  3. dissolutionthe residue was dissolved in 10 mL of water
  4. extractionextracted with EtOAc

Sources & evidence

ORD record
ord-b9dd1486914b4c3597ee97da5beba420
Source dataset
uspto-grants-2002_06
Patent number
US06403620B1

Reaction notes

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