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

HRID 1361249노트

반응식

HRID 1361249 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-bromo-pyridin-4-yl)-propan-1-ol (2.20 g 10.2 mmol) in dichloromethane (55 mL) was added Dess-Martin periodinane (5.6 g, 13 mmol). After 30 hours, and was diluted with saturated aqueous sodium carbonate (40 mL) and partially concentrated to remove the dichloromethane. The crude material was filtered through diatomaceous earth and washed with EtOAc (100 mL). The aqueous layer was separated and extracted with EtOAc (40 mL). The combined organic layers were washed with saturated aqueous sodium carbonate (40 mL) and brine (40 mL). The material was dried over magnesium sulfate, filtered and concentrated to afford 1-(2-bromo-pyridin-4-yl)-propan-1-one as a clear oil which was used without further purification.

후처리

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

출처 및 근거

ORD 기록
ord-898a893b608c447fb4090a814f2167cc
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879873B2

반응 노트

불러오는 중…