(2-(Benzyloxy)pyridin-4-yl)methanol → 2-(Benzyloxy)isonicotinaldehyde

HRID 852068Notes

Reaction equation

HRID 852068 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH2:15][OH:16])[CH:12]=[CH:11][N:10]=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[CH:14]=[C:13]([CH:12]=[CH:11][N:10]=1)[CH:15]=[O:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 16096699(2-(Benzyloxy)pyridin-4-yl)methanol

Product 1

HCID 229262712-(Benzyloxy)isonicotinaldehydeYield 89.8%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

A suspension of [2-(benzyloxy)-4-pyridyl]methanol (6.0 g) and activated manganese dioxide (30 g) in chloroform (180 mL) was heated under reflux for 2.5 hours. After the reaction solution was allowed to cool to room temperature, the manganese dioxide was filtered off and washed with ethyl acetate. The filtrate was concentrated to give the title compound as a pale brown oil (5.34 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2.5 hours
  3. filtrationthe manganese dioxide was filtered off
  4. washwashed with ethyl acetate
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-17676fa1028d4f38b483ccd90421ca33
Source dataset
uspto-grants-2007_08
Patent number
US07253178B2

Reaction notes

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