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

HRID 349938Notes

Reaction equation

HRID 349938 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([CH2:13][OH:14])[C:10]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[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[CH:12]=[C:11]([CH:13]=[O:14])[C:10]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 22930765(1-benzyl-3-benzyloxy-1H-pyrazol-4-yl)methanol

Product 1

HCID 229307681-benzyl-3-(benzyloxy)-1H-pyrazole-4-carbaldehydeYield 90%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (1-benzyl-3-benzyloxy-1H-pyrazol-4-yl)methanol (14.70 g), activated manganese dioxide (30.00 g), and tetrahydrofuran (200 ml) was stirred at room temperature for 2 hours. After the manganese dioxide was removed by filtration, the filtrate was concentrated. The crystals obtained were collected by filtration to yield 1-benzyl-3-benzyloxy-1H-pyrazole-4-carbaldehyde (13.10 g, yield: 90%). This was recrystallized from tetrahydrofuran-hexane. Melting point: 85–86° C.

Workup

  1. customAfter the manganese dioxide was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customThe crystals obtained
  4. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-4573e56c154348ed80950db373df823f
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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