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

HRID 1845573Notes

Reaction equation

HRID 1845573 reaction equation
[CH2:1]([C:3]1[CH:4]=[N:5][N:6]([CH3:17])[C:7]=1[C:8]1[CH:9]=[C:10]([C:13]([O:15]C)=[O:14])[S:11][CH:12]=1)[CH3:2].[OH-].[Na+]>O1CCCC1>[CH2:1]([C:3]1[CH:4]=[N:5][N:6]([CH3:17])[C:7]=1[C:8]1[CH:9]=[C:10]([C:13]([OH:15])=[O:14])[S:11][CH:12]=1)[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57826509HCID 57826509, compound

Product 1

HCID 578267074-(4-ethyl-1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylic AcidYield 99.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a 100 mL round-bottomed flask was added methyl 4-(4-ethyl-1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate (192 mg, 0.77 mmol) in Tetrahydrofuran (THF) (4 mL). 6N NaOH (4 mL, 24.0 mmol) was added slowly, the reaction stirred at 70° C. overnight. The reaction was cooled to room temperature, partitioned between CHCl3 and H2O and the pH of the aqueous layer adjusted to pH ˜3 by the addition of 6N HCl. The layers were separated, the organic layer dried with Na2SO4 and solvent removed affording the title compound (181 mg, quant.) used without further purification: LC-MS (ES) m/z=237 (M+H)+.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. custompartitioned between CHCl3 and H2O
  3. additionthe pH of the aqueous layer adjusted to pH ˜3 by the addition of 6N HCl
  4. customThe layers were separated
  5. dry with materialthe organic layer dried with Na2SO4 and solvent
  6. customremoved

Sources & evidence

ORD record
ord-2c9d49d1d3d445ccbbb9105112c73d23
Source dataset
uspto-grants-2015_02
Patent number
US08946278B2

Reaction notes

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