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

HRID 1961167Notes

Reaction equation

HRID 1961167 reaction equation
[Cl:1][C:2]1[O: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[O: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 57826770methyl 5-chloro-4-(1-methyl-1H-pyrazol-5-yl)-2-furancarboxylate

Product 1

HCID 578266115-chloro-4-(1-methyl-1H-pyrazol-5-yl)-2-furancarboxylic acidYield 47.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 5-chloro-4-(1-methyl-1H-pyrazol-5-yl)-2-furancarboxylate (300 mg, 1.25 mmol) in 6N sodium hydroxide (4.16 ml, 24.93 mmol) and tetrahydrofuran (5.4 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 5-chloro-4-(1-methyl-1H-pyrazol-5-yl)-2-furancarboxylic acid (267 mg, 0.59 mmol, 47% yield) as a white foam: LCMS (ES) m/e 265 (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-ac671c1b1f9d412b81c02b3e0ff364af
Source dataset
uspto-grants-2013_04
Patent number
US08410158B2

Reaction notes

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