Methyl Isobutyl Ketone → HCID 87403260, compound

HRID 2179831Notes

Reaction equation

HRID 2179831 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[CH2:12]([N+:16]1[C:24]2[CH:23]=[CH:22][C:21]3[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=3[C:19]=2[C:18]([CH3:30])([CH3:29])[C:17]=1[CH:31]=[CH:32][C:33]1[CH2:37][CH2:36][C:35](=[CH:38][CH:39]=[C:40]2[C:48]([CH3:50])([CH3:49])[C:47]3[C:46]4[CH:51]=[CH:52][CH:53]=[CH:54][C:45]=4[CH:44]=[CH:43][C:42]=3[N:41]2[CH2:55][CH2:56][CH2:57][CH3:58])[C:34]=1[S:59]([C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1)(=[O:61])=[O:60])[CH2:13][CH2:14][CH3:15].[F:68][C:69]([F:84])([S:80]([O-:83])(=[O:82])=[O:81])[C:70]([F:79])([F:78])[C:71]([F:77])([F:76])[C:72]([F:75])([F:74])[F:73].[K+].C(C(C)=O)C(C)C>O>[F:84][C:69]([F:68])([S:80]([O-:83])(=[O:82])=[O:81])[C:70]([F:78])([F:79])[C:71]([F:77])([F:76])[C:72]([F:75])([F:74])[F:73].[CH2:12]([N+:16]1[C:24]2[CH:23]=[CH:22][C:21]3[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=3[C:19]=2[C:18]([CH3:29])([CH3:30])[C:17]=1[CH:31]=[CH:32][C:33]1[CH2:37][CH2:36][C:35](=[CH:38][CH:39]=[C:40]2[C:48]([CH3:49])([CH3:50])[C:47]3[C:46]4[CH:51]=[CH:52][CH:53]=[CH:54][C:45]=4[CH:44]=[CH:43][C:42]=3[N:41]2[CH2:55][CH2:56][CH2:57][CH3:58])[C:34]=1[S:59]([C:62]1[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=1)(=[O:61])=[O:60])[CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 7909Methyl Isobutyl KetoneHCID 23675274Potassium perfluorobutanesulfonate2×HCID 86658629HCID 86658629, compound

Product 1

HCID 87403260HCID 87403260, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 0.96 g (1 mmol) of 3-butyl-2-(2-{3-[2-(3-butyl-1,1-dimethyl-1H-benzo[e]indol-2(3H)-ylidene)-ethylidene]-2-(phenylsulfonyl)cyclopent-1-en-1-yl}ethenyl)-1,1-dimethyl-1H-benzo[e]indol-3-ium p-toluenesulfonate, 0.51 g (1.5 mmol) of potassium perfluorobutanesulfonate, 20 g of water, and 20 g of methyl isobutyl ketone was stirred for 6 hours at room temperature, whereupon the organic layer was taken out. The organic layer was combined with 0.17 g (0.5 mmol) of potassium perfluorobutanesulfonate and 20 g of water and stirred overnight, whereupon the organic layer was taken out. The organic layer was washed with water and concentrated in vacuum. Diisopropyl ether was added to the residue for recrystallization. The crystal was collected and dried in vacuum, obtaining the target compound, 3-butyl-2-(2-{3-[2-(3-butyl-1,1-dimethyl-1H-benzo[e]indol-2(3H)-ylidene)ethylidene]-2-(phenylsulfonyl)cyclopent-1-en-1-yl}ethenyl)-1,1-dimethyl-1H-benzo[e]indol-3-ium perfluorobutanesulfonate. Brown crystal, 1.1 g, yield 92%.

Workup

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

Sources & evidence

ORD record
ord-655e5d9a15254debbae47c8a673c26a9
Source dataset
uspto-grants-2015_06
Patent number
US09069245B2

Reaction notes

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