Sodium Hydroxide → 2-Methyl-2-(1-(naphthalen-1-yl)-1H-pyrazol-5-yloxy)propanoic acid

HRID 386380Notes

Reaction equation

HRID 386380 reaction equation
[CH3:1][C:2]([O:9][C:10]1[N:14]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)[N:13]=[CH:12][CH:11]=1)([CH3:8])[C:3]([O:5]CC)=[O:4].[OH-].[Na+]>CO>[CH3:8][C:2]([O:9][C:10]1[N:14]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)[N:13]=[CH:12][CH:11]=1)([CH3:1])[C:3]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66820845ethyl 2-methyl-2-(1-(naphthalen-1-yl)-1H-pyrazol-5-yloxy)propanoate

Product 1

HCID 498198912-Methyl-2-(1-(naphthalen-1-yl)-1H-pyrazol-5-yloxy)propanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl 2-methyl-2-(1-(naphthalen-1-yl)-1H-pyrazol-5-yloxy)propanoate (80 mg, 0.25 mmol), aqueous sodium hydroxide solution (10%, 5 mL) and methanol (5 mL) was stirred at reflux for 2 hours. The reaction was then cooled to room temperature and the methanol removed. Water was added, neutralized with 1N HCl and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated. Purification by preparative thin layer chromatography (95% dichloromethane/5% methanol) afforded 2-Methyl-2-(1-(naphthalen-1-yl)-1H-pyrazol-5-yloxy)propanoic acid as a solid. 1H NMR (DMSO-d6, 400 MHz): δ 13.4 (s, 1H), 8.09 (m, 2H), 7.65 (m, 6H), 5.78 (d, 1H), 1.37 (s, 6H).

Workup

  1. temperatureat reflux for 2 hours
  2. customthe methanol removed
  3. additionWater was added
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated
  7. customPurification by preparative thin layer chromatography (95% dichloromethane/5% methanol)

Sources & evidence

ORD record
ord-3915c9dac646409098f4de20825675d1
Source dataset
uspto-grants-2013_02
Patent number
US08372807B2

Reaction notes

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