Pyridine → Ethyl 2-methylsulfonyloxyethylcarbamate

Participants

Reaction Steps

60 g of methanesulfonyl chloride are metered over approximately 30 minutes at 0° to +5° C. to a solution of 66.5 g of ethyl 2-hydroxyethylcarbamate, 43.5 g of pyridine and 1.9 g of 4-dimethylaminopyridine in 150 ml of methylene chloride, with stirring, and the mixture is stirred for 2 more hours at +5° C. and then for 16 hours at room temperature. The reaction mixture is filtered, the residue is washed with a small quantity of ethyl acetate, and the combined filtrates are washed with dilute hydrochloric acid and water. After the mixture has been dried over magnesium sulfate, the solvent mixture is removed completely by distillation in vacuo, which gives ethyl 2-methylsulfonyloxyethylcarbamate, nD20 1.4450.

Provenance & Evidence