Toluene → 4-(2,3,4-Trimethoxy-6-methylbenzoyl)-3-methoxy-5-trifluoromethylpyridine

HRID 242434Notes

Reaction equation

HRID 242434 reaction equation
[CH3:1][O-:2].[Na+].C1(C)C=CC=CC=1.[CH3:11][O:12][C:13]1[C:31]([O:32][CH3:33])=[C:30]([O:34][CH3:35])[CH:29]=[C:28]([CH3:36])[C:14]=1[C:15]([C:17]1[C:22]([C:23]([F:26])([F:25])[F:24])=[CH:21][N:20]=[CH:19][C:18]=1Cl)=[O:16].CN(C)P(N(C)C)N(C)C>O>[CH3:11][O:12][C:13]1[C:31]([O:32][CH3:33])=[C:30]([O:34][CH3:35])[CH:29]=[C:28]([CH3:36])[C:14]=1[C:15]([C:17]1[C:22]([C:23]([F:26])([F:25])[F:24])=[CH:21][N:20]=[CH:19][C:18]=1[O:2][CH3:1])=[O:16]

Participants

6

Reactant 4

HCID 1140TolueneHCID 15355Hexamethylphosphorous triamideHCID 10942334Sodium MethoxideHCID 121513034-(2,3,4-Trimethoxy-6-methylbenzoyl)-3-chloro-5-trifluoromethylpyridine

Product 1

HCID 121513044-(2,3,4-Trimethoxy-6-methylbenzoyl)-3-methoxy-5-trifluoromethylpyridineYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

16.4 g (304 mmol) of sodium methoxide was added to a toluene 150 ml solution of 18.5 g (47.5 mmol) of 4-(2,3,4-trimethoxy-6-methylbenzoyl)-3-chloro-5-trifluoromethylpyridine obtained in Step (c) and 16.6 ml (95.4 mmol) of hexamethylphosphorous triamide, followed by stirring under reflux with heating for 30 minutes. Water was added to terminate the reaction, and the aqueous layer was extracted with ethyl acetate. Then, the organic layer was dried over anhydrous sodium sulfate and subjected to filtration, and the solvent was distilled off under reduced pressure. The crude product was purified by silica gel column chromatography to obtain 11.7 g (yield: 64%) of 4-(2,3,4-trimethoxy-6-methylbenzoyl)-3-methoxy-5-trifluoromethylpyridine (melting point: 103 to 106° C.).

Workup

  1. temperatureunder reflux
  2. temperaturewith heating for 30 minutes
  3. customto terminate
  4. customthe reaction
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. dry with materialThen, the organic layer was dried over anhydrous sodium sulfate
  7. filtrationsubjected to filtration
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7008f1ed36274c539e22cb1e0453eaf4
Source dataset
uspto-grants-2014_02
Patent number
US08653113B2

Reaction notes

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