Reaction #465988

Reaction equation

5-cyclopropyl-3-methylthio-4-(2-methyl-4-methylsulfonylbenzoyl)isoxazole

3-chloroperbenzoic acid

→

5-cyclopropyl-3-methylsulfinyl-4-(2-methyl-4-methylsulfonylbenzoyl)isoxazole

Yield 55.8%

Solvents

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   Washwashed with aqueous sodium bicarbonate, brine
2. 2
   Otherdried
3. 3
   Otherevaporated to dryness
4. 4
   OtherThe crude product was purified by preparative thin-layer chromatography

Procedure

To a solution of 5-cyclopropyl-3-methylthio-4-(2-methyl-4-methylsulfonylbenzoyl)isoxazole (750 mg, 2.127 mmol) in dichloromethane (35 mL) was added 3-chloroperbenzoic acid (650 mg, 57-87%, Aldrich). The resulting mixture was stirred at r.t. for 2 hours, then diluted with dichloromethane, washed with aqueous sodium bicarbonate, brine, dried and evaporated to dryness. The crude product was purified by preparative thin-layer chromatography to give crystalline 5-cyclopropyl-3-methylsulfinyl-4-(2-methyl-4-methylsulfonylbenzoyl)isoxazole (436 mg), rp. 147° C. and 5-cyclopropyl-3-methylsulfonyl-4-(2-methyl-4-methylsulfonylbenzoyl)isoxazole (378 mg), m.p. 142° C.

Source