Sodium Hydroxide → 4-(4-ethyl-1-methyl-1H-pyrazol-5-yl)-5-methyl-2-thiophenecarboxylic acid

HRID 2392078Notes

Reaction equation

HRID 2392078 reaction equation
[CH2:1]([C:3]1[CH:4]=[N:5][N:6]([CH3:18])[C:7]=1[C:8]1[CH:9]=[C:10]([C:14]([O:16]C)=[O:15])[S:11][C:12]=1[CH3:13])[CH3:2].[OH-].[Na+]>O1CCCC1>[CH2:1]([C:3]1[CH:4]=[N:5][N:6]([CH3:18])[C:7]=1[C:8]1[CH:9]=[C:10]([C:14]([OH:16])=[O:15])[S:11][C:12]=1[CH3:13])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57826640methyl 4-(4-ethyl-1-methyl-1H-pyrazol-5-yl)-5-methyl-2-thiophenecarboxylate

Product 1

HCID 578265454-(4-ethyl-1-methyl-1H-pyrazol-5-yl)-5-methyl-2-thiophenecarboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 4-(4-ethyl-1-methyl-1H-pyrazol-5-yl)-5-methyl-2-thiophenecarboxylate (145 mg, 0.55 mmol) in 6N sodium hydroxide (1.8 ml, 10.97 mmol) and tetrahydrofuran (4.8 ml) was stirred at 60° C. in a sealed tube for 12 h. The resulting solution was cooled and then partitioned between H2O-DCM. The aqueous phase was adjusted to pH ˜4 and then washed several times with DCM. The combined organic fractions were dried over Na2SO4 and concentrated affording 4-(4-ethyl-1-methyl-1H-pyrazol-5-yl)-5-methyl-2-thiophenecarboxylic acid (137 mg, 0.55 mmol, 100% yield) as a yellow oil: LCMS (ES) m/e 250 (M+H)+.

Workup

  1. temperatureThe resulting solution was cooled
  2. custompartitioned between H2O-DCM
  3. washwashed several times with DCM
  4. dry with materialThe combined organic fractions were dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-675707fd0a9f43318cf1ef55f77e7bd2
Source dataset
uspto-grants-2012_09
Patent number
US08273782B2

Reaction notes

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