Pyranine → HCID 86652716, Verbindung

HRID 244291

Reaktionsgleichung

Reaktionsgleichung von HRID 244291
[Na+].[OH:2][C:3]1[CH:4]=[C:5]([S:27]([O-:30])(=[O:29])=[O:28])[C:6]2[CH:7]=[CH:8][C:9]3[C:18]4[C:17]=2[C:16]=1[CH:15]=[CH:14][C:13]=4[C:12]([S:19]([O-:22])(=[O:21])=[O:20])=[CH:11][C:10]=3[S:23]([O-:26])(=[O:25])=[O:24].[Na+].[Na+].C(N(C(C)C)CC)(C)C.Br[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][C:48]([O:50]CC)=[O:49]>CO>[C:48]([CH2:47][CH2:46][CH2:45][CH2:44][CH2:43][O:2][C:3]1[CH:4]=[C:5]([S:27]([OH:30])(=[O:29])=[O:28])[C:6]2[CH:7]=[CH:8][C:9]3[C:18]4[C:17]=2[C:16]=1[CH:15]=[CH:14][C:13]=4[C:12]([S:19]([OH:22])(=[O:21])=[O:20])=[CH:11][C:10]=3[S:23]([OH:26])(=[O:24])=[O:25])([OH:50])=[O:49]

Komponenten

5

Edukt 3

HCID 61388PyranineHCID 81531DiisopropylethylamineHCID 117544Ethyl 6-bromohexanoate

Produkt 1

HCID 86652716HCID 86652716, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 8-hydroxypyrene-1,3,6-trisulfonate sodium salt (2.6 g), diisopropylethylamine (2 g) and ethyl 6-bromohexanoate (7 g) in methanol (150 mL) was refluxed for 24 hours. The solvent was removed by rotary evaporation. The product was purified by HPLC. The isolated ethyl ester was redissolved in methanol (100 mL). About 0.5 g NaOH dissolved in 25 mL water was added. The resulting solution was stirred overnight. The methanol was removed by rotary evaporation. To the remaining aqueous solution was added acid until the solution became acidic. The precipitate was collected by filtration and dried under vacuum to give 8-(5-carboxypentoxy)pyrene-1,3,6-trisulfonic acid.

Aufarbeitung

  1. temperaturewas refluxed for 24 hours
  2. customThe solvent was removed by rotary evaporation
  3. customThe product was purified by HPLC
  4. dissolutionThe isolated ethyl ester was redissolved in methanol (100 mL)
  5. dissolutionAbout 0.5 g NaOH dissolved in 25 mL water
  6. additionwas added
  7. customThe methanol was removed by rotary evaporation
  8. additionTo the remaining aqueous solution was added acid until the solution
  9. filtrationThe precipitate was collected by filtration
  10. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-c7585a0d18a949378545ac71cf854edb
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658434B2

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