Hydrochloric Acid → [1-(4-Chlorophenyl)-5-methyl-1H-pyrazol-4-yl]methanol

HRID 1603747Notes

Reaction equation

HRID 1603747 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH3:13])=[C:11]([C:14](OCC)=[O:15])[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([CH3:13])=[C:11]([CH2:14][OH:15])[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 4282610HCID 4282610, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19606233[1-(4-Chlorophenyl)-5-methyl-1H-pyrazol-4-yl]methanolYield 91%

Procedure

To a solution of 3.2 g of ethyl 1-(4-chlorophenyl)-5-methyl-1H-pyrazole-4-carboxylate, 0.46 g of lithium aluminum hydride was added, followed by stirring for 1.5 hours at room temperature. The reaction mixture was added with a 5% aqueous solution of hydrochloric acid and then extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride, dried over magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure. The residue was subjected to chromatography on a silica gel column and then purified using gradient elution with hexane-ethyl acetate, whereby 2.45 g of the title compound were obtained (yield: 91%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with an aqueous solution of sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. custompurified
  7. washelution with hexane-ethyl acetate

Sources & evidence

ORD record
ord-c513e356f51a43ee8eda8cfaab6c0b36
Source dataset
uspto-grants-1999_11
Patent number
US05990139

Reaction notes

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