Reaction #155392

Reaction equation

4-(tert-butyldimethylsilyloxy)phenyl acridin-9-carboxylate

methyl trifluoromethanesulfonate

→

4-(tert-butyldimethylsilyloxy)phenyl 10-methylacridinium-9-carboxylate trifluoromethanesulfonate

Solvents

dichloromethane

Conditions

Workup

1. 1
   OtherInto a 50 mL round bottom flask equipped with magnetic stirrer under argon atmosphere
2. 2
   FiltrationBright yellow solid was collected by filtration
3. 3
   Washwashed with 2×1 mL of dichloromethane and air
4. 4
   Otherdried for 4 hr

Procedure

Into a 50 mL round bottom flask equipped with magnetic stirrer under argon atmosphere charged a solution of 1.6 parts of 4-(tert-butyldimethylsilyloxy)phenyl acridin-9-carboxylate in 25 mL of dichloromethane. 3.2 Parts of methyl trifluoromethanesulfonate was added to the solution and stirred for 40 hrs at room temperature. Bright yellow solid was collected by filtration, washed with 2×1 mL of dichloromethane and air dried for 4 hr to yield 1.44 parts of 4-(tert-butyldimethylsilyloxy)phenyl 10-methylacridinium-9-carboxylate trifluoromethanesulfonate having the following structure confirmed by NMR.

Source