{4H,5H,6H-pyrrolo[1,2-b]pyrazol-2-yl}methanol → 4H,5H,6H-pyrrolo(1,2-b)pyrazole-2-carbaldehyde

HRID 1158858Notes

Reaction equation

HRID 1158858 reaction equation
[N:1]1[N:2]2[CH2:10][CH2:9][CH2:8][C:3]2=[CH:4][C:5]=1[CH2:6][OH:7]>O=[Mn]=O.C(Cl)(Cl)Cl>[N:1]1[N:2]2[CH2:10][CH2:9][CH2:8][C:3]2=[CH:4][C:5]=1[CH:6]=[O:7]

Participants

4

Reactant 1

HCID 21941359{4H,5H,6H-pyrrolo[1,2-b]pyrazol-2-yl}methanol

Product 1

HCID 112864914H,5H,6H-pyrrolo(1,2-b)pyrazole-2-carbaldehyde

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6212ChloroformSolvent

Procedure

MnO2 (activated) (24.4 g) was added to the CHCl3 (350 mL) solution of (5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-2-yl)methanol (4.87 g) and refluxed for 1 h under a nitrogen atmosphere. The reaction mixture was filtered through a pad of Celite. The filtrate was reduced under reduced pressure. The residue was applied to silica gel column chromatography, then the column was eluted with n-hexane-AcOEt (1/1-1/2). The title compound was obtained as yellow oil (4.35 g, 91%).

Workup

  1. temperaturerefluxed for 1 h under a nitrogen atmosphere
  2. filtrationThe reaction mixture was filtered through a pad of Celite
  3. washthe column was eluted with n-hexane-AcOEt (1/1-1/2)

Sources & evidence

ORD record
ord-174db0ed55454fdab55623d8c8603c9c
Source dataset
uspto-grants-2010_10
Patent number
US07812014B2

Reaction notes

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