(3-(Benzyloxy)pyridin-2-yl)methanol → 3-(Benzyloxy)pyridine-2-carbaldehyde

HRID 2395067Notes

Reaction equation

HRID 2395067 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH2:15][OH:16])=[N:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH2:1]([O:8][C:9]1[C:10]([CH:15]=[O:16])=[N:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 13217540(3-(Benzyloxy)pyridin-2-yl)methanol

Product 1

HCID 133745943-(Benzyloxy)pyridine-2-carbaldehydeYield 62%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

A solution of 3-benzyloxy-2-hydroxymethylpyridine (0.25 g, 1.16 mmol) in chloroform (15 ml) was treated with manganese dioxide (0.45 g, 6.34 mmol). The reaction mixture was heated to reflux and held at reflux for 18 hours. The reaction mixture was then filtered through Celite and evaporated to give a yellow gum. This gum was purified by chromatography (EtOAc/CH2Cl2) to give 3-benzyloxy-2-pyridinecarbaldehyde as a colourless gum (0.15 g, 62%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. temperatureat reflux for 18 hours
  4. filtrationThe reaction mixture was then filtered through Celite
  5. customevaporated
  6. customto give a yellow gum
  7. customThis gum was purified by chromatography (EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-0c10ff7049394a2d97d7fba512976412
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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