Ethanol → (3-ethyl-1-methyl-1H-pyrazol-5-yl)methanol

HRID 530823Notes

Reaction equation

HRID 530823 reaction equation
[CH2:1]([C:3]1[CH:7]=[C:6]([C:8](OCC)=[O:9])[N:5]([CH3:13])[N:4]=1)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O)C.[Cl-].[NH4+]>C1COCC1>[CH2:1]([C:3]1[CH:7]=[C:6]([CH2:8][OH:9])[N:5]([CH3:13])[N:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 15131401Ethyl 3-ethyl-1-methyl-1H-pyrazole-5-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 23005574(3-ethyl-1-methyl-1H-pyrazol-5-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 3 (2 g, 0.01 mol) in THF (20 mL) was added lithium aluminum hydride (0.63 g, 0.02 mol) at 0° C. and the mixture was stirred at room temperature for 30 min. Ethanol (10 mL) and saturated aqueous ammonium chloride solution (2.0 mL) were added to the reaction mixture. The precipitated insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel chromatography (ethyl acetate:hexane=1:1) to give the title compound as a colorless oil.

Workup

  1. filtrationThe precipitated insoluble material was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-22a6b5b04f6b4770965b41f0026b769a
Source dataset
uspto-grants-2016_05
Patent number
US09353104B2

Reaction notes

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