(3-benzyloxy-1-phenyl-1H-pyrazol-5-yl)methanol → HCID 22930766, compound

HRID 2221612Notes

Reaction equation

HRID 2221612 reaction equation
[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([CH2:14][OH:15])[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[CH:13]=[C:12]([CH:14]=[O:15])[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 22930692(3-benzyloxy-1-phenyl-1H-pyrazol-5-yl)methanol

Product 1

HCID 22930766HCID 22930766, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (3-benzyloxy-1-phenyl-1H-pyrazol-5-yl)methanol (11.20 g), activated manganese dioxide (30.00 g) and tetrahydrofuran (300 mL) was stirred overnight at room temperature. The insoluble material was removed by filtration, and the mother liquid was concentrated. The residue was subjected to silica gel column chromatography to give 3-benzyloxy-1-phenyl-1H-pyrazole-5-carbaldehyde (10.10 g, yield 91%) as a pale-yellow oil from a fraction eluted with ethyl acetate-hexane (1:2, v/v).

Workup

  1. customThe insoluble material was removed by filtration
  2. concentrationthe mother liquid was concentrated

Sources & evidence

ORD record
ord-4e3ba7244554440e8361a27aae44d5df
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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