4-Toluenesulfonyl chloride → HCID 12553275, compound

Participants

Reaction Steps

To a suspension of 10.6 g (250 mmol) of sodium hydride (60% in oil) in 150 ml of DMF was added dropwise a mixture of 20 g (226 mmol) of methyl propionate and 20.4 g (340 mmol) of methyl formate under ice cooling and stirred at room temperature overnight. To the reaction mixture was added portionwise 34.6 g (181 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 11.0 g of (E)-methyl 2-methyl-3-(p-toluenesulfonyloxy)-2-propenoate.

Provenance & Evidence