Selenium Dioxide → 4-(tert-butyl)picolinaldehyde

HRID 1637730노트

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HRID 1637730 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

HCID 187996954-(tert-butyl)picolinaldehyde수율 96%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

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온도
82.5 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6c88f4d3fac14f9bb4d9c84be07569bb
출처 데이터셋
uspto-grants-2000_03
특허 번호
US06043248

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