Reaction #2275673

Reaction equation

1-butyl-2-[7-(1-butyl-1H-benzo[cd]indol-2-ylidene)hepta-1,3,5-trien-1-yl]-benzo[cd]indol-1-ium perchlorate

sodium 1,1,3,3,3-pentafluoro-2-(pivaloyloxy)propanesulfonate

water

→

1-butyl-2-[7-(1-butyl-1H-benzo[cd]indol-2-ylidene)-hepta-1,3,5-trien-1-yl]-benzo[cd]indol-1-ium 1,1,3,3,3-pentafluoro-2-(pivaloyloxy)propanesulfonate

Yield 93.0%

Solvents

methylene chloride

Conditions

Workup

1. 1
   WashThe organic layer was washed with water
2. 2
   Concentrationconcentrated in vacuum
3. 3
   Concentrationconcentrated in vacuum again
4. 4
   workup.ADDITIONDiisopropyl ether was added to the residue for recrystallization
5. 5
   OtherThe crystal was collected
6. 6
   Otherdried in vacuum

Procedure

A mixture of 1.2 g (2 mmol) of 1-butyl-2-[7-(1-butyl-1H-benzo[cd]indol-2-ylidene)hepta-1,3,5-trien-1-yl]-benzo[cd]indol-1-ium perchlorate, 6.1 g (3 mmol) of sodium 1,1,3,3,3-pentafluoro-2-(pivaloyloxy)propanesulfonate aqueous solution, 10 g of water, and 25 g of methylene chloride was stirred overnight at room temperature, whereupon the organic layer was taken out. The organic layer was washed with water, concentrated in vacuum, combined with methyl isobutyl ketone, and concentrated in vacuum again. Diisopropyl ether was added to the residue for recrystallization. The crystal was collected and dried in vacuum, obtaining the target compound, 1-butyl-2-[7-(1-butyl-1H-benzo[cd]indol-2-ylidene)-hepta-1,3,5-trien-1-yl]-benzo[cd]indol-1-ium 1,1,3,3,3-pentafluoro-2-(pivaloyloxy)propanesulfonate. Brown crystal, 2.0 g, yield 93%.

Source