Sodium Hydroxide → 4-(1-methyl-1H-pyrazol-5-yl)-2-furancarboxylic acid

HRID 2392074Notes

Reaction equation

HRID 2392074 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]([C:12]([O:14]C)=[O:13])[O: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])[O:10][CH:11]=2)=[CH:5][CH:4]=[N:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 578265722-Furancarboxylic acid, 4-(1-methyl-1H-pyrazol-5-yl)-, methyl ester

Product 1

HCID 578267434-(1-methyl-1H-pyrazol-5-yl)-2-furancarboxylic acidYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 4-(1-methyl-1H-pyrazol-5-yl)-2-furancarboxylate (124 mg, 0.60 mmol) in 6N sodium hydroxide (2.0 ml, 12.0 mmol) and tetrahydrofuran (3.0 ml) was stirred at 70° C. in a sealed tube for 2 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 4-(1-methyl-1H-pyrazol-5-yl)-2-furancarboxylic acid (54 mg, 0.28 mmol, 47% yield) as a white solid: LCMS (ES) m/e 192 (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-1581d1efe05849e7a81951d5f74c08f5
Source dataset
uspto-grants-2012_09
Patent number
US08273782B2

Reaction notes

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