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

HRID 1423045노트

반응식

HRID 1423045 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 10340Sodium Carbonate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b8591213cdfc4db8a772f88c192fd5dd
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927550B2

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