Triacetoxyperiodinane → 1-(2-Bromopyridin-4-yl)propan-1-one

HRID 1423045ノート

反応式

HRID 1423045 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([OH:11])[CH2:9][CH3:10])[CH:5]=[CH:4][N:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl.C(=O)([O-])[O-].[Na+].[Na+]>[Br:1][C:2]1[CH:7]=[C:6]([C:8](=[O:11])[CH2:9][CH3:10])[CH:5]=[CH:4][N:3]=1

参加物

5

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 866408041-(2-Bromopyridin-4-yl)-propan-1-ol

生成物 1

HCID 592773031-(2-Bromopyridin-4-yl)propan-1-one

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 10340Sodium Carbonate溶媒

実験手順

To a solution of 1-(2-bromopyridin-4-yl)-propan-1-ol (2.20 g 10.2 mmol) in dichloromethane (55 mL) is added Dess-Martin periodinane (5.6 g, 13 mmol). After 30 hours, the mixture is diluted with saturated aqueous sodium carbonate (40 mL) and partially concentrated to remove the dichloromethane. The crude material is filtered through filter agent and washed with EtOAc (100 mL). The aqueous layer is separated and extracted with EtOAc (40 mL). The combined organic layers are washed with saturated aqueous sodium carbonate (40 mL) and brine (40 mL). The material is dried over magnesium sulfate, filtered and concentrated to afford 1-(2-bromopyridin-4-yl)-propan-1-one as an oil which is used without further purification.

後処理

  1. concentrationpartially concentrated
  2. customto remove the dichloromethane
  3. filtrationThe crude material is filtered
  4. filtrationthrough filter agent
  5. washwashed with EtOAc (100 mL)
  6. customThe aqueous layer is separated
  7. extractionextracted with EtOAc (40 mL)
  8. washThe combined organic layers are washed with saturated aqueous sodium carbonate (40 mL) and brine (40 mL)
  9. dry with materialThe material is dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

出典と根拠

ORDレコード
ord-b8591213cdfc4db8a772f88c192fd5dd
出典データセット
uspto-grants-2015_01
特許番号
US08927550B2

反応ノート

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