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

HRID 1835418Notes

Reaction equation

HRID 1835418 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(=O)(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 12679HexamethylphosphoramideHCID 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 hexamethylphosphoric triamide, followed by stirring under reflux by heating for 30 minutes. Water was added thereto to terminate the reaction, the aqueous layer was extracted with ethyl acetate, and 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 thus obtained 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 (compound No. 122; m.p. 103-106° C.).

Workup

  1. temperatureunder reflux
  2. temperatureby heating for 30 minutes
  3. customto terminate
  4. customthe reaction
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. dry with materialthe 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 thus obtained
  10. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ed30b01d346b4bd58d29527f55963af1
Source dataset
uspto-grants-2004_08
Patent number
US06770662B2

Reaction notes

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