Sodium Hydroxide → 5-chloro-4-(1-methyl-1H-pyrazol-5-yl)thiophene-2-carboxylic acid

HRID 1961264Notes

Reaction equation

HRID 1961264 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([O:9]C)=[O:8])=[CH:4][C:3]=1[C:11]1[N:15]([CH3:16])[N:14]=[CH:13][CH:12]=1.[OH-].[Na+]>O1CCCC1>[Cl:1][C:2]1[S:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][C:3]=1[C:11]1[N:15]([CH3:16])[N:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57826577Methyl 5-chloro-4-(1-methyl-1H-pyrazol-5-yl)thiophene-2-carboxylate

Product 1

HCID 578263895-chloro-4-(1-methyl-1H-pyrazol-5-yl)thiophene-2-carboxylic acidYield 96.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 5-chloro-4-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate (304 mg, 1.18 mmol) in 6N sodium hydroxide (2 ml, 12 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 ˜3 and then washed several times with DCM. The combined organic fractions were dried over Na2SO4 and concentrated affording the desired product (276 mg, 1.14 mmol, 96% yield) as a yellow oil: LC-MS (ES) m/e 244 (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-c65f37678a1040c8bf045bd33d52b118
Source dataset
uspto-grants-2013_04
Patent number
US08410158B2

Reaction notes

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