Reacción #341386

Ecuación de reacción

potassium carbonate

Rongalit

5-bromomethyl-4-ethoxy-6-trifluoromethylpyrimidine

sodium hydrosulfide hydrate

3-methylsulfonyl-5-chloromethyl-5-methyl-2-isoxazoline

→

3-(4-ethoxy-6-trifluoromethylpyrimidin-5-ylmethylthio)-5-chloromethyl-5-methyl-2-isoxazoline

Rendimiento 30.3%

Disolventes

DMF

ethyl acetate

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe mixture was stirred at room temperature for 21 hours
2. 2
   Otroto give rise
3. 3
   Otroto a reaction
4. 4
   OtroAfter the completion of the reaction
5. 5
   LavadoThe resulting organic layer was washed with an aqueous sodium chloride solution
6. 6
   Secadoby drying over anhydrous magnesium sulfate
7. 7
   workup.DISTILLATIONThe resulting solution was subjected to reduced pressure distillation
8. 8
   Otroto remove the solvent
9. 9
   OtroThe residue was purified by silica gel column chromatography (solvent system: hexane-ethyl acetate)

Procedimiento

3.4 g (42.3 mmoles) of sodium hydrosulfide hydrate (purity: 70%) was added into a solution of 4.6 g (21.6 mmoles) of 3-methylsulfonyl-5-chloromethyl-5-methyl-2-isoxazoline dissolved in 70 ml of DMF. The mixture was stirred for 2 hours. Then, there were added 3.0 g (21.6 mmoles) of potassium carbonate, 3.3 g (21.6 mmoles) of Rongalit and 5-bromomethyl-4-ethoxy-6-trifluoromethylpyrimidine. The mixture was stirred at room temperature for 21 hours to give rise to a reaction. After the completion of the reaction, the reaction mixture was poured into water and extraction with ethyl acetate was conducted. The resulting organic layer was washed with an aqueous sodium chloride solution, followed by drying over anhydrous magnesium sulfate. The resulting solution was subjected to reduced pressure distillation to remove the solvent contained therein. The residue was purified by silica gel column chromatography (solvent system: hexane-ethyl acetate) to obtain 1.9 g (yield: 30.3%) of 3-(4-ethoxy-6-trifluoromethylpyrimidin-5-ylmethylthio)-5-chloromethyl-5-methyl-2-isoxazoline.

Fuente