Water → 1-butyl-2-(2-{3-[2-(1-butyl-1H-benzo[cd]indol-2-ylidene)-ethylidene]-2-phenylcyclohex-1-en-1-yl)ethenyl)-benzo[cd]indol-1-ium 1,1,3,3,3-pentafluoro-2-(pivaloyloxy)-propanesulfonate

HRID 2188493Notes

Reaction equation

HRID 2188493 reaction equation
F[B-](F)(F)F.[CH2:6]([N+:10]1[C:18]2[C:13]3[C:14](=[CH:19][CH:20]=[CH:21][C:12]=3[C:11]=1[CH:22]=[CH:23][C:24]1[CH2:29][CH2:28][CH2:27][C:26](=[CH:30][CH:31]=[C:32]3[C:40]4[CH:41]=[CH:42][CH:43]=[C:38]5[C:39]=4[C:34](=[CH:35][CH:36]=[CH:37]5)[N:33]3[CH2:44][CH2:45][CH2:46][CH3:47])[C:25]=1[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[CH:15]=[CH:16][CH:17]=2)[CH2:7][CH2:8][CH3:9].[F:54][C:55]([F:72])([S:68]([O-:71])(=[O:70])=[O:69])[CH:56]([O:61][C:62](=[O:67])[C:63]([CH3:66])([CH3:65])[CH3:64])[C:57]([F:60])([F:59])[F:58].[Na+].O>C(Cl)Cl>[F:72][C:55]([F:54])([S:68]([O-:71])(=[O:69])=[O:70])[CH:56]([O:61][C:62](=[O:67])[C:63]([CH3:65])([CH3:66])[CH3:64])[C:57]([F:58])([F:60])[F:59].[CH2:6]([N+:10]1[C:18]2[C:13]3[C:14](=[CH:19][CH:20]=[CH:21][C:12]=3[C:11]=1[CH:22]=[CH:23][C:24]1[CH2:29][CH2:28][CH2:27][C:26](=[CH:30][CH:31]=[C:32]3[C:40]4[CH:41]=[CH:42][CH:43]=[C:38]5[C:39]=4[C:34](=[CH:35][CH:36]=[CH:37]5)[N:33]3[CH2:44][CH2:45][CH2:46][CH3:47])[C:25]=1[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[CH:15]=[CH:16][CH:17]=2)[CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 962WaterHCID 752131681-butyl-2-(2-{3-[2-(1-butyl-1H-benzo[cd]indol-2-ylidene)ethylidene]-2-phenylcyclohex-1-en-1-yl)ethenyl)-benzo[cd]indol-1-ium tetrafluoroborateHCID 86616368Sodium 1,1,3,3,3-pentafluoro-2-(pivaloyloxy)propanesulfonate

Product 1

HCID 866649671-butyl-2-(2-{3-[2-(1-butyl-1H-benzo[cd]indol-2-ylidene)-ethylidene]-2-phenylcyclohex-1-en-1-yl)ethenyl)-benzo[cd]indol-1-ium 1,1,3,3,3-pentafluoro-2-(pivaloyloxy)-propanesulfonateYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2.1 g (3 mmol) of 1-butyl-2-(2-{3-[2-(1-butyl-1H-benzo[cd]indol-2-ylidene)ethylidene]-2-phenylcyclohex-1-en-1-yl)ethenyl)-benzo[cd]indol-1-ium tetrafluoroborate, 9.1 g (4.5 mmol) of sodium 1,1,3,3,3-pentafluoro-2-(pivaloyloxy)propanesulfonate aqueous solution, 20 g of water, and 50 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-(2-{3-[2-(1-butyl-1H-benzo[cd]indol-2-ylidene)-ethylidene]-2-phenylcyclohex-1-en-1-yl)ethenyl)-benzo[cd]indol-1-ium 1,1,3,3,3-pentafluoro-2-(pivaloyloxy)-propanesulfonate. Brown crystal, 2.6 g, yield 93%.

Workup

  1. washThe organic layer was washed with water
  2. concentrationconcentrated in vacuum
  3. concentrationconcentrated in vacuum again
  4. additionDiisopropyl ether was added to the residue for recrystallization
  5. customThe crystal was collected
  6. customdried in vacuum

Sources & evidence

ORD record
ord-89ed7284dcf14b3d81ab169eaf9cb50c
Source dataset
uspto-grants-2012_12
Patent number
US08323536B2

Reaction notes

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