Pyridine → 1-o-Tolyl-propane-1,2-dione

HRID 2119594Notes

Reaction equation

HRID 2119594 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8](=[O:10])[CH3:9].[Cr](Cl)([O-])(=O)=[O:13].[NH+]1C=CC=CC=1.N1C=CC=CC=1>C(Cl)Cl>[C:1]1([CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7](=[O:13])[C:8](=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 27341091-(2-Methylphenyl)propan-2-oneHCID 178418287HCID 178418287, compound

Product 1

HCID 149200021-o-Tolyl-propane-1,2-dioneYield 15.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 7 g (47.23 mmol) 1-o-Tolyl-propan-2-one, 30.5 g (0.141 mol) pyridinium chlorochromate and 11.2 g (0.141 mol) pyridine in 200 ml DCM was heated to reflux for 16 h. The mixture was filtered through a pad of silica and the filtrate was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica eluting with ethyl acetate/n-hexane 1:4. The product fractions were evaporated to yield 1.178 g (15%) of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 h
  3. filtrationThe mixture was filtered through a pad of silica
  4. customthe filtrate was evaporated under reduced pressure
  5. customThe residue was purified by flash column chromatography on silica eluting with ethyl acetate/n-hexane 1:4
  6. customThe product fractions were evaporated

Sources & evidence

ORD record
ord-d3283aa22633440c9c72b26f773945fc
Source dataset
uspto-grants-2004_02
Patent number
US06686381B2

Reaction notes

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