Hydrochloric Acid → 4-methoxy-2-(1H-pyrazol-1-yl)butanoic acid

HRID 243719Notes

Reaction equation

HRID 243719 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH:5]([N:10]1[CH:14]=[CH:13][CH:12]=[N:11]1)[C:6]([O:8]C)=[O:7].[OH-].[K+].Cl>CO.O>[CH3:1][O:2][CH2:3][CH2:4][CH:5]([N:10]1[CH:14]=[CH:13][CH:12]=[N:11]1)[C:6]([OH:8])=[O:7]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 66839386Methyl 4-methoxy-2-(1H-pyrazol-1-yl)butanoate

Product 1

HCID 579074424-methoxy-2-(1H-pyrazol-1-yl)butanoic acidYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 0.045 g (0.23 mmol) of methyl 4-methoxy-2-(1H-pyrazol-1-yl)butanoate from step A above in 2 mL of methanol was added a solution of 0.032 g (0.57 mmol) of potassium hydroxide in 0.5 mL of water. The mixture was stirred at ambient temperature for 1.5 h then acidified with a 2 N hydrochloric acid solution until a pH of 4 was achieved. The mixture was evaporated to remove all volatiles then extracted with ethyl acetate. The combined extracts were washed with brine, dried over magnesium sulfate, filtered and evaporated to dryness to afford the title compound (0.040 g, 95%). LC-MS: m/z (ES) 185 (MH)+.

Workup

  1. customThe mixture was evaporated
  2. customto remove all volatiles
  3. extractionthen extracted with ethyl acetate
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-908728a2c5e741759b270bcff7809cb2
Source dataset
uspto-grants-2014_02
Patent number
US08653260B2

Reaction notes

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