反应详情

To a suspension of 21.4 g (535 mmol) of sodium hydride (60% in oil) in 200 ml of DMF was added dropwise a mixture of 25.8 g (214 mmol) of methyl 2-(methylthio)acetate and 26.5 g (428 mmol) of methyl formate under ice cooling and stirred at room temperature overnight. To the reaction mixture was added portionwise 27.0 g (141 mmol) of p-toluenesulfonyl chloride under ice cooling and stirred at room temperature for 1 hour. After dilution with tert-butyl methyl ether, the solution was washed sequentially with water and saturated NaCl solution, dried over anhydrous MgSO4, and concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1) to obtain 9.72 g of methyl 2-(methylthio)-3-(p-toluenesulfonyloxy)-2-propenoate and 1.88 g of methyl 3-chloro-2-(methylthio)-2-propenoate.

1. additionwas added dropwise
2. stirringstirred at room temperature for 1 hour
3. washAfter dilution with tert-butyl methyl ether, the solution was washed sequentially with water and saturated NaCl solution
4. dry with materialdried over anhydrous MgSO4
5. concentrationconcentrated
6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1)