(4H,5H,6H,7H-pyrazolo(1,5-a)pyridin-2-yl)methanol → 4,5,6,7-Tetrahydropyrazolo[1,5-a]pyridine-2-carbaldehyde

HRID 2216566Notes

Reaction equation

HRID 2216566 reaction equation
[N:1]1[N:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:4]2=[CH:3][C:2]=1[CH2:10][OH:11]>O=[Mn]=O.C(Cl)(Cl)Cl>[N:1]1[N:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:4]2=[CH:3][C:2]=1[CH:10]=[O:11]

Participants

4

Reactant 1

HCID 11845786(4H,5H,6H,7H-pyrazolo(1,5-a)pyridin-2-yl)methanol

Product 1

HCID 118454214,5,6,7-Tetrahydropyrazolo[1,5-a]pyridine-2-carbaldehyde

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6212ChloroformSolvent

Procedure

MnO2 (activated) (3.36 g) was added to the CHCl3 (44 mL) solution of (4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-2-yl)methanol (673 mg) 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 (2/1–1/2). The titled compound was obtained as pale yellow oil (510 mg, 77%).

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 (2/1–1/2)

Sources & evidence

ORD record
ord-f4b3829d47314834b869381c8a72e287
Source dataset
uspto-grants-2006_09
Patent number
US07112582B2

Reaction notes

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