Réaction #84221

Équation de réaction

OXONE

2-(5-chloro-6-trifluoromethyl-1H-indol-2-yl)-1-(4-fluoro-phenylsulfanyl)-propan-2-ol

water

water

→

title product

2-(5-Chloro-6-trifluoromethyl-1H-indol-2-yl)-1-(4-fluoro-benzenesulfonyl)-propan-2-ol

Solvants

dichloromethane

dichloromethane

Conditions de réaction

Traitement

1. 1
   Autrethe layers were separated
2. 2
   Extractionthe aqueous layer was extracted with dichloromethane
3. 3
   LavageThe combined organic layers were washed with water, twice with 10% sodium thiosulfate solution and brine
4. 4
   Séchagedried over magnesium sulfate
5. 5
   FiltrationThe magnesium sulfate was filtered off
6. 6
   Concentrationthe filtrate was concentrated
7. 7
   Autrepre-absorbed onto silica gel
8. 8
   Autrepurified by column chromatography
9. 9
   Lavageeluting with 80% diethyl ether/pentane

Mode opératoire

To a solution of 2-(5-chloro-6-trifluoromethyl-1H-indol-2-yl)-1-(4-fluoro-phenylsulfanyl)-propan-2-ol (0.42 g, 1.04 mmol) in dichloromethane (10 mL) was added water (10 mL). The solution was stirred rapidly and tetrabutylammonium hydrogensulfate (12 mg, 0.035 mmol) was added followed by OXONE® (1.02 g, 1.66 mmol). The reaction mixture turned bright yellow and was allowed to proceed overnight at room temperature. The reaction mixture was diluted with water and dichloromethane, the layers were separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with water, twice with 10% sodium thiosulfate solution and brine, then dried over magnesium sulfate. The magnesium sulfate was filtered off and the filtrate was concentrated and pre-absorbed onto silica gel and purified by column chromatography eluting with 80% diethyl ether/pentane to yield the title product as a solid.

Source