Ethylene Glycol → 6-[1,3]Dioxolan-2-yl-pyridine-2-carbaldehyde

HRID 931117

Reaktionsgleichung

Reaktionsgleichung von HRID 931117
[N:1]1[C:6]([CH:7]=[O:8])=[CH:5][CH:4]=[CH:3][C:2]=1[CH:9]=[O:10].[CH2:11](O)[CH2:12][OH:13].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[O:8]1[CH2:11][CH2:12][O:13][CH:7]1[C:6]1[N:1]=[C:2]([CH:9]=[O:10])[CH:3]=[CH:4][CH:5]=1

Komponenten

5

Edukt 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 794852,6-Diformylpyridine

Produkt 1

HCID 193617196-[1,3]Dioxolan-2-yl-pyridine-2-carbaldehydeAusbeute 60,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

To a solution of pyridine-2,6-dicarbaldehyde (5 g, 37.4 mmol) in benzene (100 mL) was added ethylene glycol (1.1 g, 18.5 mmol) and p-toluenesulfonic acid (0.3 g, 1.8 mmol). The reaction mixture was equipped with a dean stark condenser and refluxed for 15 min. The reaction mixture was concentrated under reduced pressure and the resulting crude was purified via column chromatography to afford 6-(1,3-dioxolan-2-yl)picolinaldehyde (2 g, 30%). MS (ES+) (M+H) 180.0495

Aufarbeitung

  1. customThe reaction mixture was equipped with a dean stark condenser
  2. temperaturerefluxed for 15 min
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe resulting crude was purified via column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ed6d39517b1a40e2ab51394c8e3290f7
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296745B2

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