Aluminium lithium hydride → HCID 57497168, compound

HRID 403267Notes

Reaction equation

HRID 403267 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-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[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 57497168HCID 57497168, compoundYield 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 mmole) in THF (5 ml) was added at 0° C. a solution of LiAlH4 (1M in THF, 0.35 ml) and stirring was continued for 30 min. The mixture was quenched at −15° C. with saturated aqueous KHSO4, extracted with diethyl ether, the organic layer was dried, evaporated and the residue purified by chromatography on silica gel using cyclohexane/AcOEt (4:1) to give the title compound (71 mg) as a pale yellow oil.

Workup

  1. customThe mixture was quenched at −15° C. with saturated aqueous KHSO4
  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-f9e232fc222c4a98997b084201a5a705
Source dataset
uspto-grants-2014_06
Patent number
US08748418B2

Reaction notes

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