Methyl Isobutyl Ketone → HCID 131733079, compound

HRID 2179832Notes

Reaction equation

HRID 2179832 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].[N-:68]([S:76]([C:79]([F:82])([F:81])[F:80])(=[O:78])=[O:77])[S:69]([C:72]([F:75])([F:74])[F:73])(=[O:71])=[O:70].[Li+].C(C(C)=O)C(C)C>O>[N-:68]([S:69]([C:72]([F:75])([F:73])[F:74])(=[O:71])=[O:70])[S:76]([C:79]([F:82])([F:81])[F:80])(=[O:78])=[O:77].[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 3816071Lithium bis((trifluoromethyl)sulfonyl)azanide2×HCID 86658629HCID 86658629, compound

Product 1

HCID 131733079HCID 131733079, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 2.87 g (3 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, 1.31 g (4.5 mmol) of lithium bis(trifluoromethanesulfonyl)imide, 40 g of water, and 40 g of methyl isobutyl ketone was stirred for 8 hours at room temperature, whereupon the organic layer was taken out. The organic layer was combined with 0.43 g (1.5 mmol) of lithium bis(trifluoromethanesulfonyl)imide and 40 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 bis(trifluoromethylsulfonyl)imide. Brown crystal, 2.9 g, yield 87%.

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-152be1b6d37247bc9cfc3619f60a256d
Source dataset
uspto-grants-2015_06
Patent number
US09069245B2

Reaction notes

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