反応 #40895

反応方程式

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

溶媒

chloroform

chloroform

反応条件

後処理

1. 1
   workup.STIRRINGby stirring at room temperature for 3 hours
2. 2
   抽出followed by extraction with ethyl acetate
3. 3
   洗浄The organic layer was washed in turn with an aqueous saturated sodium hydrogen carbonate solution, water and saturated saline
4. 4
   乾燥dried over anhydrous magnesium sulfate
5. 5
   濃縮concentrated
6. 6
   その他The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=95:5→91:9)

実験手順

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).

出典