Aluminium lithium hydride → HCID 59589344, compound

HRID 577159Notes

Reaction equation

HRID 577159 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:9]1[CH:13]=[C:12]([CH2:14][CH3:15])[C:11]([C:16](OC)=[O:17])=[N:10]1)[CH3:8]>C1COCC1>[CH2:7]([N:9]1[CH:13]=[C:12]([CH2:14][CH3:15])[C:11]([CH2:16][OH:17])=[N:10]1)[CH3:8]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66820740HCID 66820740, compound

Product 1

HCID 59589344HCID 59589344, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (433 mg, 11.4 mmol) was stirred in anhydrous THF (50 mL). A solution of methyl 1,4-diethyl-1H-pyrazole-3-carboxylate (1.28 g, 7.6 mmol) in anhydrous THF (10 mL) was added at 0° C., and then stirred at room temperature for 1.5 hours. The reaction was quenched with an aqueous solution of sodium hydroxide and extracted 5 times with ethyl acetate. The combined organic phase was washed with brine and dried over sodium sulfate. After evaporation of the solvent, (1,4-diethyl-1H-pyrazol-3-yl)methanol was obtained (710 mg, 65% yield) and used in the next step without further purification.

Workup

  1. customThe reaction was quenched with an aqueous solution of sodium hydroxide
  2. extractionextracted 5 times with ethyl acetate
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-a7356b7afd664384850838114f426550
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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