Methyl triflate → 4-(Tert-butyldimethylsilyloxy)phenyl 10-methylacridinium-9-carboxylate trifluoromethanesulfonate

HRID 1034586Notes

Reaction equation

HRID 1034586 reaction equation
[CH:1]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([C:13]=2[C:15]([O:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])=[CH:20][CH:19]=2)=[O:16])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[F:32][C:33]([F:40])([F:39])[S:34]([O:37]C)(=[O:36])=[O:35]>ClCCl>[F:32][C:33]([F:40])([F:39])[S:34]([O-:37])(=[O:36])=[O:35].[CH3:33][N+:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:13]([C:15]([O:17][C:18]2[CH:19]=[CH:20][C:21]([O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:26])[CH3:27])=[CH:22][CH:23]=2)=[O:16])=[C:14]2[C:5]=1[CH:4]=[CH:3][CH:2]=[CH:1]2

Participants

4

Reactant 2

HCID 9526Methyl triflateHCID 21972276HCID 21972276, compound

Product 1

HCID 866153714-(Tert-butyldimethylsilyloxy)phenyl 10-methylacridinium-9-carboxylate trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

  1. customInto a 50 mL round bottom flask equipped with magnetic stirrer under argon atmosphere
  2. filtrationBright yellow solid was collected by filtration
  3. washwashed with 2×1 mL of dichloromethane and air
  4. customdried for 4 hr

Sources & evidence

ORD record
ord-b6810416db3547f3b5176b2ef8b9bf9e
Source dataset
uspto-grants-2013_10
Patent number
US08546150B2

Reaction notes

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