Reaktion #49885

Reaktionsgleichung

diethylaminosulfur trifluoride

1-(diethylcarbamoyl)-3-(2-methyl-3-chlorophenylsulfonyl)-4-hydroxymethylpyrazole

1-(Diethylcarbamoyl)-3-(2-methyl-3-chlorophenylsulfonyl)-4-hydroxymethylpyrazole

water

→

title compound

Ausbeute 95.0%

1-(Diethylcarbamoyl)-3-(2-methyl-3-chlorophenylsulfonyl)-4-fluoromethylpyrazole

Ausbeute 95.0%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with methylene chloride
2. 2
   WaschenThe extract was washed with a saturated aqueous solution of sodium chloride
3. 3
   Trocknendried over anhydrous sodium sulfate
4. 4
   Einengenconcentrated by evaporation under reduced pressure
5. 5
   SonstigeThe concentrate was purified by column chromatography through silica gel
6. 6
   Wascheneluted with an 8:1 by volume mixture of hexane and ethyl acetate

Vorschrift

20 μl of diethylaminosulfur trifluoride were added at 0° C. to a solution of 54 mg of 1-(diethylcarbamoyl)-3-(2-methyl-3-chlorophenylsulfonyl)-4-hydroxymethylpyrazole (prepared as described in Example 10) in 1.8 ml of methylene chloride, and the resulting mixture was stirred for 1 hour. At the end of this time, the reaction mixture was poured into water and extracted with methylene chloride. The extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated by evaporation under reduced pressure. The concentrate was purified by column chromatography through silica gel, eluted with an 8:1 by volume mixture of hexane and ethyl acetate, to afford 51 mg (yield 95%) of the title compound as an oil.

Quelle