Selenium Dioxide → 4-(tert-butyl)picolinaldehyde

HRID 1637730Notes

Reaction equation

HRID 1637730 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH2:11][OH:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Se](=O)=O>O1CCOCC1.ClCCl>[C:1]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH:11]=[O:12])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 24007Selenium DioxideHCID 18799645(4-(tert-Butyl)pyridin-2-yl)methanol

Product 1

HCID 187996954-(tert-butyl)picolinaldehydeYield 96%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
82.5 °C

Procedure

4-t-Butyl-2-hydroxymethyl-pyridine (4.13 g, 25 mmole) is dissolved in 75 ml dioxane in a 200 ml one neck round bottom flask under nitrogen. The solution is treated with selenium dioxide (1.53 g, 13.75 mmole) and the reaction is warmed to 80-85° C. for 1 h. The mixture is cooled, diluted with dichloromethane, and is filtered through celite. The filter cake is washed well with dichloromethane and the filtrate is concentrated to an amber oil. The crude oil is passed through a 50 g plug of silica gel (230-400 mesh), eluting with 20% acetone/hexane, while collecting 100 ml fractions. Fractions 1-3 are combined and concentrated to give 3.91 g (96%) of 4-t-Butyl-2-pyridine-carboxaldehyde as a light amber oil.

Workup

  1. temperatureThe mixture is cooled
  2. filtrationis filtered through celite
  3. washThe filter cake is washed well with dichloromethane
  4. concentrationthe filtrate is concentrated to an amber oil
  5. washeluting with 20% acetone/hexane
  6. customwhile collecting 100 ml fractions
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6c88f4d3fac14f9bb4d9c84be07569bb
Source dataset
uspto-grants-2000_03
Patent number
US06043248

Reaction notes

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