2,2,2-Trifluoroethanol → 2,2,2-Trifluoroethyl 2-naphthalenesulfonate

Participants

Reaction Steps

To a stirred solution of 25.0 parts of 2,2,2-trifluoroethanol in 175 parts of N,N-diethylethanamine were added portionwise 62.2 parts of 2-naphthalenesulfonyl chloride and then a mixture of 1.5 parts of N,N-dimethyl-4-pyridinamine and 25 parts of ethyl acetate. After stirring overnight at room temperature, the reaction mixture was filtered and the filtrate was evaporated. The residue was stirred in water. The solid was filtered off and dissolved in dichloromethane. This solution was dried, filtered and evaporated. The residue was successively triturated with petroleumether and crystallized from 2-propanol. The product was filtered off and dried, yielding 65.3 parts (89%) of 2,2,2-trifluoroethyl 2-naphthalenesulfonate; mp. 72.7° C. (interm. 12).

Provenance & Evidence