Reacción #2275673

ord-e9ae28b42d7042d39ec3aa1f2415d371

Ecuación de reacción

CCCCn1c(=CC=CC=CC=CC2=[N+](CCCC)c3cccc4cccc2c34)c2cccc3cccc1c32.[O-][Cl+3]([O-])([O-])[O-]
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
CC(C)(C)C(=O)OC(C(F)(F)F)C(F)(F)S(=O)(=O)[O-].[Na+]
sodium 1,1,3,3,3-pentafluoro-2-(pivaloyloxy)propanesulfonate
O
water
CC(C)(C)C(=O)OC(C(F)(F)F)C(F)(F)S(=O)(=O)[O-].CCCCn1c(=CC=CC=CC=CC2=[N+](CCCC)c3cccc4cccc2c34)c2cccc3cccc1c32
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
Rendimiento 93.0%

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    LavadoThe organic layer was washed with water
  2. 2
    Concentraciónconcentrated in vacuum
  3. 3
    Concentraciónconcentrated in vacuum again
  4. 4
    workup.ADDITIONDiisopropyl ether was added to the residue for recrystallization
  5. 5
    OtroThe crystal was collected
  6. 6
    Otrodried in vacuum

Procedimiento

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%.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08323536B2uspto-grants-2012_12