p-Toluenesulfonic acid → 2-Phenyl-4-(pyrid-3-yl)-5-(2-bromophenyl)-1,3-dioxolane

HRID 1613647Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1613647
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([OH:17])(O)[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Br:15])[CH:2]=1.C[O:19][CH:20](OC)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClC1C=CC=CC=1.C1(C)C=CC=CC=1>[C:21]1([CH:20]2[O:17][CH:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[CH:8]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[Br:15])[O:19]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 62375Benzaldehyde dimethyl acetalHCID 197741971-(Pyrid-3-yl)-2-(2-bromophenyl)-ethanediol

Produkt 1

HCID 197742082-Phenyl-4-(pyrid-3-yl)-5-(2-bromophenyl)-1,3-dioxolane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 18994452Chlorobenzene tolueneLösungsmittel

Versuchsvorschrift

37 g (0.1258 mol) of 1-(pyrid-3-yl)-2-(2-bromophenyl)-ethanediol and 38.5 g (0.2516 mol) of benzaldehyde dimethyl acetal were refluxed together in 440 ml of 10:1 chlorobenzene/toluene with 1 g of p-toluenesulfonic acid. The resulting methanol was distilled off as an azeotrope with toluene. After the end of the reaction, the chlorobenzene was distilled off under reduced pressure and the product wa purified by chromatography over silica gel.

Aufarbeitung

  1. distillationThe resulting methanol was distilled off as an azeotrope with toluene
  2. customAfter the end of the reaction
  3. distillationthe chlorobenzene was distilled off under reduced pressure
  4. customthe product wa purified by chromatography over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-44799372e3b448cca7597c756cfd0536
Quelldatensatz
uspto-grants-1993_03
Patentnummer
US05194441

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