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

HRID 1295250Notes

Reaction equation

HRID 1295250 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), active manganese dioxide (15.00 g) and tetrahydrofuran (75 ml) was stirred overnight at room temperature. Manganese dioxide was filtered off and the filtrate was concentrated. The residue was subjected to silica gel column chromatography, and 3-benzyloxy-1-phenyl-1H-pyrazole-4-carbaldehyde (5.03 g, yield 90%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (2:1, volume ratio). The crystals were recrystallized from tetrahydrofuran-hexane. melting point: 153–154° C.

Workup

  1. filtrationManganese dioxide was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-d7d5d39c5abb43d2b27de1bec8fc9fd5
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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