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

HRID 2392235Notes

Reaction equation

HRID 2392235 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]([C:14]([O:16]C)=[O:15])[S:10][C:11]=2[CH2:12][CH3:13])=[C:5]([CH3:18])[CH:4]=[N:3]1.[OH-].[Na+]>O1CCCC1>[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]([C:14]([OH:16])=[O:15])[S:10][C:11]=2[CH2:12][CH3:13])=[C:5]([CH3:18])[CH:4]=[N:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57826857methyl 4-(1,4-dimethyl-1H-pyrazol-5-yl)-5-ethyl-2-thiophenecarboxylate

Product 1

HCID 578266384-(1,4-dimethyl-1H-pyrazol-5-yl)-5-ethyl-2-thiophenecarboxylic acidYield 96.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 4-(1,4-dimethyl-1H-pyrazol-5-yl)-5-ethyl-2-thiophenecarboxylate (488 mg, 1.85 mmol) in 6N sodium hydroxide (3.08 ml, 18.5 mmol) and Tetrahydrofuran (10 ml) was stirred at 70° C. in a sealed tube for 1 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 the title compound as a yellow foam (448 mg, 1.79 mmol, 96% yield) as a yellow oil: LCMS (ES) m/e 251 (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-609a65794b8349e1a663ad20458c7a7f
Source dataset
uspto-grants-2012_09
Patent number
US08273782B2

Reaction notes

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