반응 #1470450

반응 방정식

diisopropylether

m-chloroperbenzoic acid

5-Cyclopropyl-3-methylsulfanyl-4-(2-methanesulfonyl-4-trifluoromethylbenzoyl)isoxazole

ethyl acetate hexane

→

5-cyclopropyl-3-methylsulfinyl-4-(2-methanesulfonyl-4-trifluoromethylbenzoyl)isoxazole

수율 75.9%

용매

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   workup.ADDITIONis added in portions
2. 2
   여과the resulting precipitate filtered off
3. 3
   추출The dichloromethane phase is successively extracted with 5% aqueous NaHCO3 solution, twice with water and 15% aqueous sodium chloride solution
4. 4
   기타After the organic phase has been separated off
5. 5
   건조it is dried over magnesium sulfate
6. 6
   기타The raw product obtained

실험 절차

1.0 g (2.5 mmol) 5-Cyclopropyl-3-methylsulfanyl-4-(2-methanesulfonyl-4-trifluoromethylbenzoyl)isoxazole is dissolved in 12 ml dichloromethane. The solution is then cooled to a temperature of −5° C., and 0.62 g (70%, 2.5 mmol) m-chloroperbenzoic acid is added in portions. After 18 hours' agitation at a temperature of 0 to 5° C., the reaction mixture is diluted with dichloromethane and the resulting precipitate filtered off. The dichloromethane phase is successively extracted with 5% aqueous NaHCO3 solution, twice with water and 15% aqueous sodium chloride solution. After the organic phase has been separated off, it is dried over magnesium sulfate. The raw product obtained is subjected to flash chromatography on silica gel using ethyl acetate/hexane (first 1:1 then 2:1) as eluent. After stirring in a little diisopropylether, 0,8 g of 5-cyclopropyl-3-methylsulfinyl-4-(2-methanesulfonyl-4-trifluoromethylbenzoyl)isoxazole is obtained in the form of crystals with a melting point of 153-155° C. 1H-NMR (CDCl3, ppm): 0.96-1.16 (m, 2H), 1.2-1.36 (m, 1H), 1.32-1.4 (m, 2H), 3.12 (s, 3H), 3.32 (s, 3H), 7.72 (d, 1H), 8.05 (d, 1H), 8.41 (s, 1H).

출처