Triacetoxyperiodinane → HCID 59278472, compound

HRID 1423060Notes

Reaction equation

HRID 1423060 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([OH:11])[CH2:9][CH3:10])=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C1COCC1.ClCCl.C(=O)([O-])[O-].[K+].[K+].O=[Mn]=O>[Br:1][C:2]1[N:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9][CH3:10])=[CH:4][CH:3]=1

Participants

7

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86640808HCID 86640808, compound

Product 1

HCID 59278472HCID 59278472, compound

Reagents, catalysts & solvents 4

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 11430Potassium CarbonateSolvent

Procedure

To a solution of 1-(6-bromopyridin-3-yl)-propan-1-ol (12.9 g, 59.9 mmol) in THF (200 mL) is added 85% activated Mn02 (6.4 g, 63 mmol) and the mixture is stirred overnight. The reaction is monitored by TLC (EtOAc-hexanes 4:6) indicating starting material and a new less polar product. To the mixture is added additional 85% activated MnO2 (6.0 g, 58.66 mmol) and the mixture stirred for 2 days. The reaction is monitored by TLC (EtOAc-hexanes 3:7) indicating starting material is still present. The mixture is warmed at reflux for 6 hours. The mixture is filtered through filter agent and concentrated. The residue is diluted with dichloromethane and Dess-Martin periodinane (19 g, 44.8 mmol) is added. After 1 hour, the mixture is diluted with saturated aqueous potassium carbonate (200 mL) and concentrated. The resulting solid is collected by filtration washing with water and dried. The solid is suspended in dichloromethane and filtered and the filtrate is passed through a pad of silica gel eluting with ether to afford 1-(6-bromopyridin-3-yl)-propan-1-one as a solid.

Workup

  1. stirringthe mixture stirred for 2 days
  2. temperatureThe mixture is warmed
  3. temperatureat reflux for 6 hours
  4. filtrationThe mixture is filtered
  5. filtrationthrough filter agent
  6. concentrationconcentrated
  7. additionis added
  8. waitAfter 1 hour
  9. concentrationconcentrated
  10. filtrationThe resulting solid is collected by filtration
  11. washwashing with water
  12. customdried
  13. filtrationfiltered

Sources & evidence

ORD record
ord-022bac2cbfdb4d1f8cdc73ab1b54a38d
Source dataset
uspto-grants-2015_01
Patent number
US08927550B2

Reaction notes

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