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

HRID 2047352Notes

Reaction equation

HRID 2047352 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]([C:12]([O:14]C)=[O:13])[S:10][CH:11]=2)=[CH:5][CH:4]=[N:3]1.[OH-].[Na+]>O1CCCC1>[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]([C:12]([OH:14])=[O:13])[S:10][CH:11]=2)=[CH:5][CH:4]=[N:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57826540Methyl 4-(1-methyl-1H-pyrazol-5-yl)thiophene-2-carboxylate

Product 1

HCID 578264554-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylic AcidYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 4-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate (3 g, 13.50 mmol) in 6N sodium hydroxide (22.50 ml, 135 mmol) and tetrahydrofuran (27.0 ml) was stirred in a sealed tube at 70° C. After 1 h, the solution was partitioned between H2O-DCM and the pH of the aqueous layer was adjusted to ˜3. The aqueous layer was washed several times with DCM and the combined organic fractions were dried over Na2SO4, concentrated affording 4-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylic acid (2.8 g, 13.45 mmol, 100% yield) as a yellow solid which was used directly without further purification: LCMS (ES) m/e 209 (M+H)+.

Workup

  1. customthe solution was partitioned between H2O-DCM
  2. washThe aqueous layer was washed several times with DCM
  3. dry with materialthe combined organic fractions were dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1aa37e5ab42c4346a5bc7fb967719d95
Source dataset
uspto-grants-2013_11
Patent number
US08592475B2

Reaction notes

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