1,1,3,3,5,5,5-Heptamethyltrisiloxane → HCID 178504321, compound

HRID 876193Notes

Reaction equation

HRID 876193 reaction equation
[CH2:1]([N:4]=[C:5]([C:7]1[C:24]2=[C:25]3[C:14]([C:15]4[C:26]5[C:19](=[CH:20][CH:21]=[CH:22][C:23]2=5)[CH:18]=[CH:17][CH:16]=4)=[CH:13][CH:12]=[C:11]([C:27]([OH:29])=[O:28])[C:10]3=[C:9]([C:30]([OH:32])=[O:31])[C:8]=1[C:33](=[N:35][CH2:36][CH:37]=[CH2:38])[OH:34])[OH:6])[CH:2]=[CH2:3].[CH3:39][Si:40]([CH3:50])([CH3:49])[O:41][Si:42]([CH3:48])([CH3:47])[O:43][SiH:44]([CH3:46])[CH3:45]>C1(C)C=CC=CC=1>[CH3:39][Si:40]([CH3:49])([CH3:50])[O:41][Si:42]([CH3:48])([CH3:47])[O:43][Si:44]([CH2:3][CH2:2][CH2:1][N:4]=[C:5]([C:7]1[C:24]2=[C:25]3[C:14]([C:15]4[C:26]5[C:19](=[CH:20][CH:21]=[CH:22][C:23]2=5)[CH:18]=[CH:17][CH:16]=4)=[CH:13][CH:12]=[C:11]([C:27]([OH:29])=[O:28])[C:10]3=[C:9]([C:30]([OH:32])=[O:31])[C:8]=1[C:33](=[N:35][CH2:36][CH2:37][CH2:38][Si:44]([CH3:46])([CH3:45])[O:43][Si:42]([CH3:48])([CH3:47])[O:41][Si:40]([CH3:50])([CH3:49])[CH3:39])[OH:34])[OH:6])([CH3:45])[CH3:46]

Participants

4

Reactant 2

HCID 761701,1,3,3,5,5,5-HeptamethyltrisiloxaneHCID 178457715HCID 178457715, compound2×

Product 1

HCID 178504321HCID 178504321, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.03 g (2.19 mmol) of perylene tetracarboxylic acid bis(allylimide) (compound (6), m=1, n=1) and 1.53 g (6.87 mmol) of 1,1,1,3,3,5,5-heptamethyl trisiloxane were dissolved in 100 ml of toluene, and 20 μl of a Karstedt catalyst (2 mol/l solution in xylene) was thereafter added thereto, which was then refluxed for 5 hours. The reaction solution thus obtained was then cooled and filtered, and the toluene was distilled off from a filtrate. The crude product thus obtained was purified by silica gel column chromatography (eluent: dichloromethane→dichloromethane-ethyl acetate (50:1)). The resultant crude product was dissolved in dichloromethane and re-precipitated with methanol. Thus, 1.51 g (1.65 mmol) of a red powder was obtained as an intended compound (1-1). A yield of the compound (1-1) was 75.3%. Values obtained by instrumental analysis of the compound (1-1) are shown below.

Workup

  1. temperaturewhich was then refluxed for 5 hours
  2. customThe reaction solution thus obtained
  3. temperaturewas then cooled
  4. filtrationfiltered
  5. distillationthe toluene was distilled off from a filtrate
  6. customThe crude product thus obtained
  7. customwas purified by silica gel column chromatography (eluent: dichloromethane→dichloromethane-ethyl acetate (50:1))
  8. dissolutionThe resultant crude product was dissolved in dichloromethane
  9. customre-precipitated with methanol

Sources & evidence

ORD record
ord-70af0e72bb454d04b2d336c6e7e5aaaa
Source dataset
uspto-grants-2015_03
Patent number
US08987044B2

Reaction notes

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