Dimethyl Sulfoxide → Butanoic acid, 2-[bis(methylthio)methylene]-3-oxo-, ethyl ester

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Reaction Steps

In 100 ml of dimethyl sulfoxide is dissolved 50.0 g of ethyl acetoacetate. To the solution is added at room temperature 53.1 g of potassium carbonate, and the mixture is stirred for 30 minutes. To the resultant is added, while keeping the inner temperature at 10° C., 29.3 g of carbon disulfide dropwise over a period of 30 minutes, followed by stirring at 10° C. for one hour. To the mixture is further added 120.0g of methyl iodide dropwise at the same temperature over a period of 30 minutes, which is stirred at the same temperature for one hour. The inner temperature is reverted to room temperature, then the reaction mixture is stirred for one hour, poured into 200 ml of ice water, and extracted with dichloromethane. The extract is washed with water, dried and concentrated to give 66.0 g of the title compound as a light brown oil.

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