Reaktion #329616

Reaktionsgleichung

sodium methoxide

toluene

4-(2,3,4-trimethoxy-6-methylbenzoyl)-3-chloro-5-trifluoromethylpyridine

hexamethylphosphorous triamide

→

4-(2,3,4-trimethoxy-6-methylbenzoyl)-3-methoxy-5-trifluoromethylpyridine

Ausbeute 64.0%

Lösungsmittel

Water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder reflux
2. 2
   Temperaturwith heating for 30 minutes
3. 3
   Sonstigeto terminate
4. 4
   Sonstigethe reaction
5. 5
   Extraktionthe aqueous layer was extracted with ethyl acetate
6. 6
   TrocknenThen, the organic layer was dried over anhydrous sodium sulfate
7. 7
   Filtrationsubjected to filtration
8. 8
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
9. 9
   SonstigeThe crude product was purified by silica gel column chromatography

Vorschrift

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.).

Quelle