Trifluoromethanesulfonic acid, lithium salt → HCID 15252133, compound

Participants

Reaction Steps

A solution of lithium triflate (3.81 g, 24.4 mmol) in dry acetonitrile (20 cm3) was added to a stirred slurry of 1-chloromethyl-4-aza-1-azoniabicyclo[2,2,2]-octane chloride (4.81 g, 24.4 mmol) in the same solvent (25 cm3) at ambient temperature under dry nitrogen. After being stirred overnight, the reaction mixture was filtered to remove lithium chloride, and the latter was washed with dry acetonitrile (20 cm3). Evaporation of the washings and the filtrate left a yellowish white solid which was recrystallised from an ethanol-diethyl ether mixture to provide white 1-chloromethyl-4-aza-1-azoniabicyclo [2,2,2]octane triflate (6.68 g, 21.5 mmol, 88%), m.p. 152° C. (dec.; charring commenced at 130° C.), δF (solution in D2O; ext. CF3CO2H ref.) 0.1 (s; CF3SO3-) p.p.m., δH (same soln.) 3.29 (m; 3×CH2), 3.57 (m; 3×CH2), 5.12 (s; CH2Cl) ppm (residual H in D2O, 4.75 p.p.m.).

Provenance & Evidence