2-Methyl-1-(pyridin-3-yl)propan-1-ol → 2-Methyl-1-(pyridin-3-yl)propan-1-one

HRID 1747524Notes

Reaction equation

HRID 1747524 reaction equation
[CH3:1][CH:2]([CH3:11])[CH:3]([C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1)[OH:4]>ClCCl.[O-2].[O-2].[Mn+4]>[CH3:1][CH:2]([CH3:11])[C:3]([C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1)=[O:4]

Participants

4

Reactant 1

HCID 135614132-Methyl-1-(pyridin-3-yl)propan-1-ol

Product 1

HCID 122813372-Methyl-1-(pyridin-3-yl)propan-1-oneYield 81%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

In dichloromethane (60.0 mL) was dissolved 2-methyl-1-(pyridin-3-yl)propan-1-ol (2.16 g, 14.3 mmol) obtained in Step 1. Manganese dioxide (107 g) was added and the mixture was stirred at room temperature for 7 hours. After the reaction mixture was filtered through Celite, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to give 2-methyl-1-(pyridin-3-yl)propan-1-one (1.72 g, 81% yield).

Workup

  1. filtrationAfter the reaction mixture was filtered through Celite
  2. customthe solvent in the filtrate was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-c55eaad45f974d9cbf38123d24b823f2
Source dataset
uspto-grants-2015_10
Patent number
US09150569B2

Reaction notes

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