반응 #474451

반응 방정식

EDTA

Ethyl 5-bromo-3-(tetrahydro-2H-thiopyran-3-yl)-1H-indole-7-carboxylate

oxone

sodium bicarbonate

→

title compound

수율 71.0%

Ethyl 5-bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-3-yl)-1H-indole-7-carboxylate

수율 71.0%

용매

water

1,2-Dimethoxyethane

water

반응 조건

후처리

1. 1
   추출extracted with dichloromethane
2. 2
   세척The combined organics were washed with water 2×
3. 3
   세척The combined organics were washed with water, brine
4. 4
   건조dried with MgSO4
5. 5
   농축concentrated
6. 6
   기타The crude compound was purified by Combiflash silica column chromatography

실험 절차

Ethyl 5-bromo-3-(tetrahydro-2H-thiopyran-3-yl)-1H-indole-7-carboxylate (0.375 g, 1.02 mmol) was dissolved in 1,2-Dimethoxyethane (DME) (25 mL). A solution of 0.0004M EDTA (7 mL) was added followed by the portion-wise addition of a suspension of oxone (1.88 g, 3.05 mmol) and sodium bicarbonate (0.855 g, 10.18 mmol) in 7 mL water. The reaction was stirred for 3 hours at room temperature. The reaction was diluted with water and extracted with dichloromethane. The combined organics were washed with water 2×. The combined aqueous layers were backwashed with dichloromethane. The combined organics were washed with water, brine, dried with MgSO4 and concentrated. The crude compound was purified by Combiflash silica column chromatography using 0-10% ethylacetate/dichloromethane on silica to give 0.290 g (71%) of the title compound.

출처