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

HRID 1845641Notes

Reaction equation

HRID 1845641 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][C:12]=1[Cl:17].[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][C:12]=1[Cl:17]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 578265502-Furancarboxylic acid, 5-chloro-4-(4-chloro-1-methyl-1H-pyrazol-5-yl)-, methyl ester

Product 1

HCID 578264792-Furancarboxylic acid, 5-chloro-4-(4-chloro-1-methyl-1H-pyrazol-5-yl)-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 5-chloro-4-(4-chloro-1-methyl-1H-pyrazol-5-yl)-2-furancarboxylate (224 mg, 0.82 mmol) in 6N sodium hydroxide (1.36 ml, 8.2 mmol) and tetrahydrofuran (5 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 (201 mg, 0.77 mmol, 94° A yield) as a yellow oil: LCMS (ES) m/e 262 (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-833dc58e079342f18d05d8118826bed1
Source dataset
uspto-grants-2015_02
Patent number
US08946278B2

Reaction notes

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