Ethylene Glycol → 2-Bromo-4-(1,3-dioxolan-2-yl)pyridine

HRID 1110973Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1110973
[Br:1][C:2]1[CH:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][N:3]=1.[CH2:10](O)[CH2:11][OH:12].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C1C=CC=CC=1.O>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)[CH:5]=[CH:4][N:3]=1

Komponenten

7

Edukt 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 27629912-Bromo-4-pyridinecarboxaldehyde

Produkt 1

HCID 146965072-Bromo-4-(1,3-dioxolan-2-yl)pyridineAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

60 g of 2-bromo-4-pyridinecarboxaldehyde was dissolved in 600 ml of benzene, and 40 g of ethylene glycol and 6 g of p-toluenesulfonic acid were put in the solution. The mixture was heated under reflux for 18 hours while water was removed by using a Dean-Stark trap. After the reaction, the reaction mixture was made basic by adding ice and a saturated aqueous solution of sodium hydrogen carbonate. The organic layer was washed with water and dried. The solvent was evaporated. The residue was distilled to give 60 g (yield 82%) of 2-bromo-4-(1,3-dioxolan-2-yl)pyridine.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. customwas removed
  3. customAfter the reaction
  4. additionby adding ice
  5. washThe organic layer was washed with water
  6. customdried
  7. customThe solvent was evaporated
  8. distillationThe residue was distilled

Quellen und Nachweise

ORD-Eintrag
ord-4404f8a68aec4a05ad8e810df7ebb21c
Quelldatensatz
uspto-grants-1990_12
Patentnummer
US04977267

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