(3-benzyloxy-1-phenyl-1H-pyrazol-4-yl)methanol → 3-benzyloxy-1-phenyl-1H-pyrazole-4-carbaldehyde

HRID 2221609Notes

Reaction equation

HRID 2221609 reaction equation
[CH2:1]([O:8][C:9]1[C:13]([CH2:14][OH:15])=[CH:12][N:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[O-2].[O-2].[Mn+4].O1CCCC1>[CH2:1]([O:8][C:9]1[C:13]([CH:14]=[O:15])=[CH:12][N:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 22930694(3-benzyloxy-1-phenyl-1H-pyrazol-4-yl)methanol

Product 1

HCID 229307603-benzyloxy-1-phenyl-1H-pyrazole-4-carbaldehydeYield 90.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (3-benzyloxy-1-phenyl-1H-pyrazol-4-yl)methanol (5.61 g), activated manganese dioxide (15.00 g) and tetrahydrofuran (75 mL) was stirred overnight at room temperature. Manganese dioxide was removed by filtration, and the filtrate was concentrated. The residue was subjected to silica gel column chromatography to give 3-benzyloxy-1-phenyl-1H-pyrazole-4-carbaldehyde (5.03 g, yield 90%) as colorless crystals from a fraction eluted with ethyl acetate-hexane (2:1, v/v). The crystals were recrystallized from tetrahydrofuran-hexane. melting point: 153-154° C.

Workup

  1. customManganese dioxide was removed by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-1b69b7e57c484ce7a519841c9b23e741
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

Loading…