[1-(4-benzyloxybenzyl)-3-(4-benzyloxybenzyloxy)-1H-pyrazol-4-yl]methanol → 1-(4-benzyloxybenzyl)-3-(4-benzyloxybenzyloxy)-1H-pyrazole-4-carbaldehyde

HRID 349945Notes

Reaction equation

HRID 349945 reaction equation
[CH2:1]([O:8][C:9]1[CH:38]=[CH:37][C:12]([CH2:13][N:14]2[CH:18]=[C:17]([CH2:19][OH:20])[C:16]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:25][CH:24]=3)=[N:15]2)=[CH:11][CH: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:38]=[CH:37][C:12]([CH2:13][N:14]2[CH:18]=[C:17]([CH:19]=[O:20])[C:16]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:25][CH:24]=3)=[N:15]2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 69423856[1-(4-benzyloxybenzyl)-3-(4-benzyloxybenzyloxy)-1H-pyrazol-4-yl]methanol

Product 1

HCID 230247931-(4-benzyloxybenzyl)-3-(4-benzyloxybenzyloxy)-1H-pyrazole-4-carbaldehydeYield 95.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [1-(4-benzyloxybenzyl)-3-(4-benzyloxybenzyloxy)-1H-pyrazol-4-yl]methanol (6.84 g), activated manganese dioxide (14.00 g), and tetrahydrofuran (70 ml) was stirred at room temperature for one hour. After the manganese dioxide was removed by filtration, the filtrate was concentrated. The crystals obtained were collected by filtration to yield 1-(4-benzyloxybenzyl)-3-(4-benzyloxybenzyloxy)-1H-pyrazole-4-carbaldehyde (6.50 g, yield: 95%). This was recrystallized from tetrahydrofuran-hexane. Melting point: 138–139° 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-f342aa9ba49642148599c76f822f040d
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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