Triacetoxyperiodinane → HCID 59277303, compound

HRID 559751Notes

Reaction equation

HRID 559751 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-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.

Workup

  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

Sources & evidence

ORD record
ord-535f64d8f5db4721975435acf92443c0
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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