Methanol → potassium 2-(4-(1H-pyrazol-1-yl)phenyl)-2-methoxyacetate

HRID 1798564Notes

Reaction equation

HRID 1798564 reaction equation
[N:1]1([C:6]2[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.[CH:14](Br)(Br)Br.[OH-:18].[K+:19].[CH3:20][OH:21]>O1CCOCC1>[N:1]1([C:6]2[CH:13]=[CH:12][C:9]([CH:10]([O:11][CH3:14])[C:20]([O-:21])=[O:18])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.[K+:19]

Participants

6

Reactant 4

HCID 887Methanol2×HCID 5558BromoformHCID 14797Potassium HydroxideHCID 27764774-(1H-Pyrazol-1-yl)benzaldehyde

Product 1

HCID 67388986potassium 2-(4-(1H-pyrazol-1-yl)phenyl)-2-methoxyacetate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 4-(1H-pyrazol-1-yl)benzaldehyde (1.3 g, 7.55 mmol) and bromoform (0.85 mL, 9.75 mmol) in MeOH (10 mL) and dioxane (10 mL) was added dropwise a solution of potassium hydroxide (2.2 g, 39 mmol) in MeOH (10 mL) over 15 minutes. Stirring was then continued for 23 hours. The mixture was filtered through Celite, rinsed through with EtOAc and concentrated under reduced pressure to yield potassium 2-(4-(1H-pyrazol-1-yl)phenyl)-2-methoxyacetate as a light yellow solid (3.2 g) that was used without further purification. See U.S. Pat. No. 7,129,238.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washrinsed through with EtOAc
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a580a519076a4e308063d9a85f2955db
Source dataset
uspto-grants-2013_01
Patent number
US08343970B2

Reaction notes

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