Lithium Hydroxide → HCID 15655153, compound

HRID 2067952Notes

Reaction equation

HRID 2067952 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[N:7][N:8]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[C:9]=1[CH2:10][O:11][CH3:12])=[O:4].[OH-].[Li+]>O.CO.C1COCC1>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([N:8]2[C:9]([CH2:10][O:11][CH3:12])=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=[N:7]2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 15655149HCID 15655149, compound

Product 1

HCID 15655153HCID 15655153, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of 1-(4-chloro-phenyl)-5-methoxymethyl-1H-pyrazole-4-carboxylic acid methyl ester (6.0 g, 21 mmol) in H2O-MeOH-THF (1:1:2) is added lithium hydroxide (620 mg, 26 mmol). After stiffing at room temperature for 18 h, the reaction mixture is concentrated in vacuo and purified by flash chromatography on silica gel (eluted with 15 to 100% EtOAc/hexanes) to afford 1-(4-chloro-phenyl)-5-methoxymethyl-1H-pyrazole-4-carboxylic acid as a white solid (3.8 g, 66%).

Workup

  1. concentrationthe reaction mixture is concentrated in vacuo
  2. custompurified by flash chromatography on silica gel (eluted with 15 to 100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d559a660a6134243bf886b38a2c03d96
Source dataset
uspto-grants-2012_10
Patent number
US08293917B2

Reaction notes

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