Phosgene → Carbamate

Participants

Reaction Steps

An alcohol was dissolved in dichloromethane or tetrahydrofunan under argon atmosphere, followed by addition of an appropriate amount of a base (triethylamine, diisopropyl ethyl amine, pyridine or 4-(N,N-dimethyl)aminopyridine). To the reaction mixture, a solution of solid phosgene in dichloromethane or tetrahydrofunan was added dropwisely under ice bath, then the reaction was allowed to react for half an hour under ice bath and then for a few hours at room temperature to obtain a chlorofomate. After the addition of an appropriate amount of the base (triethylamine, diisopropylethylamine, pyridine or 4-(N,N-dimethyl)aminopyridine) under ice bath, a solution of the compound B in dichloromethane or tetrahydrofunan was slowly added dropwisely. The reaction was allowed to react for half an hour under ice bath and then for three hours at room temperature. After the reaction was completed, saturated sodium bicarbonate solution was added therein and the reaction mixture was extracted with dichloromethane. Then the combined organic phase was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and then treated with an anhydride or an acyl chloride in the presence of a base (triethylamine, diisopropylethylamine, pyridine or 4-(N,N-dimethyl)aminopyridine) to give carbamate derivative F.

Provenance & Evidence