Triacetoxyperiodinane → HCID 59277303, compound

HRID 1423045Notes

Reaction equation

HRID 1423045 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

HCID 59277303HCID 59277303, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b8591213cdfc4db8a772f88c192fd5dd
Source dataset
uspto-grants-2015_01
Patent number
US08927550B2

Reaction notes

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