Selenium Dioxide → 4-(tert-butyl)picolinaldehyde

HRID 1637730ノート

反応式

HRID 1637730 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

HCID 187996954-(tert-butyl)picolinaldehyde収率 96%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
82.5 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6c88f4d3fac14f9bb4d9c84be07569bb
出典データセット
uspto-grants-2000_03
特許番号
US06043248

反応ノート

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