1-(6-Bromo-2-pyridinyl)-1-pentanol → 1-(6-Bromopyridin-2-yl)pentan-1-one

HRID 1391774Notes

Reaction equation

HRID 1391774 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH:8]([OH:13])[CH2:9][CH2:10][CH2:11][CH3:12])[CH:5]=[CH:4][CH:3]=1>C(Cl)(Cl)Cl.[O-2].[Mn+2]>[Br:1][C:2]1[N:7]=[C:6]([C:8](=[O:13])[CH2:9][CH2:10][CH2:11][CH3:12])[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 586299071-(6-Bromo-2-pyridinyl)-1-pentanol

Product 1

HCID 586298071-(6-Bromopyridin-2-yl)pentan-1-oneYield 62.2%

Reagents, catalysts & solvents 2

HCID 160959Manganese oxideCatalystHCID 6212ChloroformSolvent

Procedure

To a stirring solution of 1-(6-bromo-2-pyridinyl)-1-pentanol (1.01 g, 4.15 mmol) in chloroform (27 mL) was added manganese oxide (14.24 g, 0.16 mol) portion-wise over 4 h. The mixture was then left to stir for an additional 3.5 h and was then filtered through celite placed directly on the top of a SPE (silica, 20 g cartridge) eluting with chloroform. The filtrate was reduce under vacuum and then purified further by SPE (silica, 20 g cartridge) eluting with cyclohexane:EtOAc (gradient 100:1 to 5:1) afforded the title compound as an oil (625 mg).

Workup

  1. waitThe mixture was then left
  2. filtrationwas then filtered through celite
  3. washeluting with chloroform
  4. custompurified further by SPE (silica, 20 g cartridge)
  5. washeluting with cyclohexane

Sources & evidence

ORD record
ord-4b6bb5c3f566461f9d013386517b42cf
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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