(2,3,4-Trimethoxy-6-methylphenyl)(5-chloro-2-methoxy-4-methyl-3-pyridyl)methanol → Pyriofenone

HRID 243773Notes

Reaction equation

HRID 243773 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=[C:5]([CH3:13])[C:4]=1[CH:14]([C:16]1[C:17]([O:24][CH3:25])=[N:18][CH:19]=[C:20]([Cl:23])[C:21]=1[CH3:22])[OH:15]>[O-2].[O-2].[Mn+4].C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=[C:5]([CH3:13])[C:4]=1[C:14]([C:16]1[C:17]([O:24][CH3:25])=[N:18][CH:19]=[C:20]([Cl:23])[C:21]=1[CH3:22])=[O:15]

Participants

4

Reactant 1

HCID 23082593(2,3,4-Trimethoxy-6-methylphenyl)(5-chloro-2-methoxy-4-methyl-3-pyridyl)methanol

Product 1

HCID 23082663PyriofenoneYield 91.7%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

4 g of active manganese dioxide was added to a toluene 15 ml solution of 0.64 g (1.7 mmol) of (2,3,4-trimethoxy-6-methylphenyl)(5-chloro-2-methoxy-4-methyl-3-pyridyl)methanol, followed by stirring under reflux with heating for 1 hour. The reaction solution was subjected to filtration on the pad of celite, and the solvent was distilled off under reduced pressure to obtain 0.57 g (yield: 90%) of 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-chloro-2-methoxy-4-methylpyridine (melting point 94.5 to 95.5° C.)

Workup

  1. temperatureunder reflux
  2. temperaturewith heating for 1 hour
  3. filtrationThe reaction solution was subjected to filtration on the pad of celite
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-f9c6be5e6f6b4ecb9ad4a753e174f1d6
Source dataset
uspto-grants-2014_02
Patent number
US08653277B2

Reaction notes

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