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

HRID 559751ノート

反応式

HRID 559751 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-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.

後処理

  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

出典と根拠

ORDレコード
ord-535f64d8f5db4721975435acf92443c0
出典データセット
uspto-grants-2011_11
特許番号
US08063065B2

反応ノート

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