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Hydrochloric Acid → 3,3'-((2,7-bis(naphthalen-1-yl(phenyl)amino)-9H-fluorene-9,9-diyl)bis(butane-4,1-diyl))dibenzaldehyde

HRID 42390
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 42390
[O:1]1CCO[CH:2]1[C:6]1[CH:7]=[C:8]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]2([CH2:63][CH2:64][CH2:65][CH2:66][C:67]3[CH:72]=[CH:71][CH:70]=[C:69]([CH:73]4OCC[O:74]4)[CH:68]=3)[C:28]3[CH:27]=[C:26]([N:29]([C:36]4[C:45]5[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=5)[CH:39]=[CH:38][CH:37]=4)[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH:25]=[CH:24][C:23]=3[C:22]3[C:17]2=[CH:18][C:19]([N:46]([C:53]2[C:62]4[C:57](=[CH:58][CH:59]=[CH:60][CH:61]=4)[CH:56]=[CH:55][CH:54]=2)[C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)=[CH:20][CH:21]=3)[CH:9]=[CH:10][CH:11]=1.Cl>CC(C)=O>[C:36]1([N:29]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:26]2[CH:25]=[CH:24][C:23]3[C:22]4[C:17](=[CH:18][C:19]([N:46]([C:53]5[C:62]6[C:57](=[CH:58][CH:59]=[CH:60][CH:61]=6)[CH:56]=[CH:55][CH:54]=5)[C:47]5[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=5)=[CH:20][CH:21]=4)[C:16]([CH2:63][CH2:64][CH2:65][CH2:66][C:67]4[CH:68]=[C:69]([CH:70]=[CH:71][CH:72]=4)[CH:73]=[O:74])([CH2:15][CH2:14][CH2:13][CH2:12][C:8]4[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=4)[CH:2]=[O:1])[C:28]=3[CH:27]=2)[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:39]=[CH:38][CH:37]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 580284899,9-bis(4-(3-(1,3-dioxolan-2-yl)phenyl)butyl)-N2,N7-di(naphthalen-1-yl)-N2,N7-diphenyl-9H-fluorene-2,7-diamine

Produkt 1

HCID 580284653,3'-((2,7-bis(naphthalen-1-yl(phenyl)amino)-9H-fluorene-9,9-diyl)bis(butane-4,1-diyl))dibenzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To 1-liter three-neck round bottom flask equipped with a magnetic stir bar and an addition funnel was transferred a solution of 9,9-bis(4-(3-(1,3-dioxolan-2-yl)phenyl)butyl)-N2,N7-di(naphthalen-1-yl)-N2,N7-diphenyl-9H-fluorene-2,7-diamine (12.3 g) in acetone (500 mL). Hydrochloric acid solution (61.0 mL, 2.0M) was transferred to the addition funnel atop the reaction flask by syringe. The acid solution was added to the reaction dropwise with vigorous stirring. The reaction was allowed to stir for an additional 30 minutes following the addition of acid. Reaction completion was confirmed by thin-layer chromatography and solvent was removed by rotary evaporation. Ethyl acetate (750 mL) was added to the resulting mixture and this solution was washed with DI water (5×200 mL). The organic fraction was collected and dried over anhydrous magnesium sulfate. Solids were removed by gravity filtration. Silica gel was added to the solution and solvent was removed by rotary evaporation leaving the crude material adsorbed to silica. Crude product was initially purified by flash column chromatography using ethyl acetate/hexane as an eluent. The resulting material was dissolved in a minimum amount of acetone and precipitated into cold methanol (3×750 mL). The solids collected by vacuum filtration were dried and determined to be pure product by NMR.

Aufarbeitung

  1. customTo 1-liter three-neck round bottom flask equipped with a magnetic stir bar and an addition funnel
  2. additionThe acid solution was added to the reaction dropwise with vigorous stirring
  3. additionthe addition of acid
  4. customReaction completion
  5. customwas removed by rotary evaporation
  6. additionEthyl acetate (750 mL) was added to the resulting mixture
  7. washthis solution was washed with DI water (5×200 mL)
  8. customThe organic fraction was collected
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customSolids were removed by gravity filtration
  11. additionSilica gel was added to the solution and solvent
  12. customwas removed by rotary evaporation

Quellen und Nachweise

ORD-Eintrag
ord-a6bb1a2a643f4625bdd2c5a6b8abc4b6
Quelldatensatz
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08535974B2

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