Reaction #465987

Reaction equation

3-cyclopropyl-2-(bis(methylthio)methylene)-1-(2-chloro-4-methylsulfonylphenyl)propan-1,3-dione

hydroxylamine hydrochloride

sodium acetate

→

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

Yield 79.6%

Solvents

ethanol

Conditions

Workup

1. 1
   Otherevaporated to dryness
2. 2
   Washwashed with water
3. 3
   Otherdried
4. 4
   Otherevaporated to dryness
5. 5
   OtherThe crude product was purified by preparative Thin-layer chromatography

Procedure

To a solution of 3-cyclopropyl-2-(bis(methylthio)methylene)-1-(2-chloro-4-methylsulfonylphenyl)propan-1,3-dione (123 mg, 0.304 mmol) in ethanol (15 mL) was added hydroxylamine hydrochloride (23 mg, 0.334 mmol) and sodium acetate (25 mg, 0.304 mmol). The resulting mixture was stirred at r.t. overnight, then evaporated to dryness and the residue was taken up in ethyl acetate, washed with water, dried and evaporated to dryness. The crude product was purified by preparative Thin-layer chromatography to give 90 mg of crystalline 5-cyclopropyl-3-methylthio-4-(2-chloro-4-methylsulfonylbenzoyl)isoxazole, m.p. 141° C.

Source