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

HRID 2392164Notes

Reaction equation

HRID 2392164 reaction equation
[CH:1]1([C:4]2[CH:5]=[N:6][N:7]([CH3:18])[C:8]=2[C:9]2[CH:10]=[C:11]([C:14]([O:16]C)=[O:15])[S:12][CH:13]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>O1CCCC1>[CH:1]1([C:4]2[CH:5]=[N:6][N:7]([CH3:18])[C:8]=2[C:9]2[CH:10]=[C:11]([C:14]([OH:16])=[O:15])[S:12][CH:13]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57826471HCID 57826471, compound

Product 1

HCID 578266304-(4-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylic AcidYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a 100 mL round-bottomed flask was added methyl 4-(4-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate (0.42 g, 1.60 mmol) in Tetrahydrofuran (THF) (8 ml). 6N NaOH (8 ml, 48.0 mmol) was added slowly and the reaction stirred at 70° C. overnight. The reaction was cooled and partitioned between CHCl3 and H2O. The pH of the aqueous layer was adjusted to ˜3 by the addition of 6N HCl. The layers were separated, the organic layer dried with Na2SO4 and solvent removed affording the title compound (0.42 g, 1.60 mmol, 95%) which was used without further purification: LC-MS (ES) m/z=249 (M+H)+.

Workup

  1. temperatureThe reaction was cooled
  2. custompartitioned between CHCl3 and H2O
  3. additionThe pH of the aqueous layer was adjusted to ˜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-06ecb1312e9a4be9a182a58090f09bf4
Source dataset
uspto-grants-2012_09
Patent number
US08273782B2

Reaction notes

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