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

HRID 1295221Notes

Reaction equation

HRID 1295221 reaction equation
[CH2:1]([O:8][C:9]1[C:13]([CH2:14][OH:15])=[CH:12][N:11]([CH3:16])[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]([CH3:16])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 22930776(3-benzyloxy-1-methyl-1H-pyrazol-4-yl)methanol

Product 1

HCID 229307233-(benzyloxy)-1-methyl-1H-pyrazole-4-carbaldehydeYield 81.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (3-benzyloxy-1-methyl-1H-pyrazol-4-yl)methanol (18.40 g), active manganese dioxide (40.00 g) and tetrahydrofuran (200 ml) was stirred at room temperature for 9 hrs. Manganese dioxide was filtered off and the filtrate was concentrated. The residue was subjected to silica gel column chromatography, and 3-benzyloxy-1-methyl-1H-pyrazole-4-carbaldehyde (14.80 g, yield 81%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (2:1, volume ratio).

Workup

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

Sources & evidence

ORD record
ord-94b8d23fa42d4fce93be60b37627eca5
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

Loading…