4,5-Dichloro-2-methoxy-alpha-(2,3,4-trimethoxy-6-methylphenyl)-3-pyridinemethanol → (4,5-Dichloro-2-methoxy-3-pyridinyl)(2,3,4-trimethoxy-6-methylphenyl)methanone

HRID 243761Notes

Reaction equation

HRID 243761 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[Cl:22])[OH:15]>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[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[Cl:22])=[O:15]

Participants

4

Reactant 1

HCID 230826084,5-Dichloro-2-methoxy-alpha-(2,3,4-trimethoxy-6-methylphenyl)-3-pyridinemethanol

Product 1

HCID 23082660(4,5-Dichloro-2-methoxy-3-pyridinyl)(2,3,4-trimethoxy-6-methylphenyl)methanoneYield 65%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

13.8 g (159 mmol) of manganese dioxide was added to a solution having 4.66 g (12.0 mmol) of (2,3,4-trimethoxy-6-methylphenyl)(4,5-dichloro-2-methoxy-3-pyridyl)methanol obtained in Step (f) dissolved in 30 ml of toluene, followed by reflux with heating for 2 hours. After cooling to room temperature, manganese dioxide was removed by filtration on the pad of celite, and toluene was distilled off under reduced pressure, followed by purification by silica gel column chromatography to obtain 2.98 g (yield: 65%) of 3-(2,3,4-trimethoxy-6-methylbenzoyl)-4,5-dichloro-2-methoxypyridine.

Workup

  1. temperatureby reflux
  2. temperaturewith heating for 2 hours
  3. custommanganese dioxide was removed by filtration on the pad of celite, and toluene
  4. distillationwas distilled off under reduced pressure
  5. customfollowed by purification by silica gel column chromatography

Sources & evidence

ORD record
ord-cced509fc3884091b3cc87679f19cca7
Source dataset
uspto-grants-2014_02
Patent number
US08653277B2

Reaction notes

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