반응 #40895

반응 방정식

ethyl 4-{7-bromo-1-[2-(ethyloxy)-2-oxoethyl]-1H-indol-3-yl}butanoate

dimethyl disulfide

sulfuryl chloride

sodium hydrogen carbonate

→

titled compound

ethyl 4-[7-bromo-1-[2-(ethyloxy)-2-oxoethyl]-2-(methylthio)-1H-indol-3-yl]butanoate

용매

chloroform

chloroform

반응 조건

후처리

1. 1
   workup.STIRRINGby stirring at room temperature for 3 hours
2. 2
   추출followed by extraction with ethyl acetate
3. 3
   세척The organic layer was washed in turn with an aqueous saturated sodium hydrogen carbonate solution, water and saturated saline
4. 4
   건조dried over anhydrous magnesium sulfate
5. 5
   농축concentrated
6. 6
   기타The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=95:5→91:9)

실험 절차

To a chloroform (0.8 mL) solution of dimethyl disulfide (30 mg), sulfuryl chloride (34 mg) was added at −15° C. and the mixture was stirred at −5° C. for 1.5 hours. To the reaction mixture, a chloroform (0.5 mL) solution of the compound prepared in Example 43, namely, ethyl 4-{7-bromo-1-[2-(ethyloxy)-2-oxoethyl]-1H-indol-3-yl}butanoate (100 mg) was added at −78° C., followed by stirring at room temperature for 3 hours. To the reaction mixture, an aqueous saturated sodium hydrogen carbonate solution was added under ice cooling, followed by extraction with ethyl acetate. The organic layer was washed in turn with an aqueous saturated sodium hydrogen carbonate solution, water and saturated saline, dried over anhydrous magnesium sulfate and then concentrated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=95:5→91:9) to obtain the titled compound having the following physical properties (70 mg).

출처