(1-benzyl-5-phenyl-1H-pyrazol-4-yl)methanol → 1-benzyl-5-phenyl-1H-pyrazole-4-carbaldehyde

HRID 349920Notes

Reaction equation

HRID 349920 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:11]([CH2:19][OH:20])[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[O-2].[O-2].[Mn+4].O1CCCC1>[CH2:1]([N:8]1[C:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[C:11]([CH:19]=[O:20])[CH:10]=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 23025093(1-benzyl-5-phenyl-1H-pyrazol-4-yl)methanol

Product 1

HCID 230247651-benzyl-5-phenyl-1H-pyrazole-4-carbaldehydeYield 75.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (1-benzyl-5-phenyl-1H-pyrazol-4-yl)methanol (9.76 g), activated manganese dioxide (20.0 g), and tetrahydrofuran (200 ml) was stirred at room temperature for 12 hours. After the manganese dioxide was removed by filtration, the filtrate was concentrated. The residue was subjected to silica gel column chromatography, and 1-benzyl-5-phenyl-1H-pyrazole-4-carbaldehyde (7.30 g, yield: 75%) was obtained as colorless crystals from the fraction eluted with ethyl acetate-hexane (1:2, volume ratio). This was recrystallized from ethyl acetate-hexane. Melting point: 99–100° C.

Workup

  1. customAfter the manganese dioxide was removed by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-be07b4fe177f4bf5b4927409ad6e7339
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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