Sodium Hydroxide → 5-(3-benzofuran-2-yl-phenyl)-2-methyl-2H-pyrazole-3-carboxylic acid

HRID 1011896Notes

Reaction equation

HRID 1011896 reaction equation
C[O:2][C:3]([C:5]1[N:6]([CH3:25])[N:7]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]2[O:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[CH:17]=2)[CH:9]=1)=[O:4].[OH-].[Na+]>CS(C)=O.O>[O:20]1[C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[CH:17]=[C:16]1[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:8]1[CH:9]=[C:5]([C:3]([OH:4])=[O:2])[N:6]([CH3:25])[N:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67315543HCID 67315543, compound

Product 1

HCID 673151845-(3-benzofuran-2-yl-phenyl)-2-methyl-2H-pyrazole-3-carboxylic acidYield 97.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A suspension of 0.90 g (2.71 mmol) of 5-(3-benzofuran-2-yl-phenyl)-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester (6′A) in 8.50 ml of DMSO was treated at RT with 1.35 ml (5.42 mmol) of aqueous 1N NaOH. After 2 h, reaction was diluted with chilled water and extracted 1× with Et2O. The water phase was acidified with aqueous 10% KHSO4 and extracted with Et2O (2×). These organic phases were washed with aqueous 10% NaCl, dried (Na2SO4) and evaporated to give 0.84 g (97%) of the title compound as white powder. MS: 317.1 (M−H−).

Workup

  1. customreaction
  2. extractionextracted 1× with Et2O
  3. extractionextracted with Et2O (2×)
  4. washThese organic phases were washed with aqueous 10% NaCl
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-7b12852ffa06416ca62ceeeaef0b77aa
Source dataset
uspto-grants-2011_07
Patent number
US07977358B2

Reaction notes

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