Aluminium lithium hydride → 4-chloro-1-(difluoromethyl)-1H-pyrazole-3-carbaldehyde

HRID 1626110Notes

Reaction equation

HRID 1626110 reaction equation
CON(C)[C:4]([C:6]1[C:10]([Cl:11])=[CH:9][N:8]([CH:12]([F:14])[F:13])[N:7]=1)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Cl:11][C:10]1[C:6]([CH:4]=[O:5])=[N:7][N:8]([CH:12]([F:13])[F:14])[CH:9]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 580828434-Chloro-1-difluoromethyl-1H-pyrazole-3-carboxylic acid methoxy-methyl-amide

Product 1

HCID 574971684-chloro-1-(difluoromethyl)-1H-pyrazole-3-carbaldehydeYield 57.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chloro-1-difluoromethyl-1H-pyrazole-3-carboxylic acid methoxy-methyl-amide (164 mg, 0.68 mmol) in tetrahydrofuran (5 ml) was added at 0° C. a solution of lithium aluminiumhydride (1M in tetrahydrofuran, 0.35 ml) and stirring was continued for 30 minutes. The mixture was quenched at −15° C. with a saturated aqueous solution of potassium hydrogensulphate and extracted with diethyl ether. The organic layer was dried, evaporated and the residue purified by chromatography on silica gel using cyclohexane/ethyl acetate (4:1) as the eluent to give the title compound (71 mg) as a pale yellow oil.

Workup

  1. customThe mixture was quenched at −15° C. with a saturated aqueous solution of potassium hydrogensulphate
  2. extractionextracted with diethyl ether
  3. customThe organic layer was dried
  4. customevaporated
  5. customthe residue purified by chromatography on silica gel

Sources & evidence

ORD record
ord-59a228720faf49a5a4114db711b9083a
Source dataset
uspto-grants-2014_07
Patent number
US08785436B2

Reaction notes

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