Ethylene Glycol → 2-(1,3-Dioxolan-2-yl)-3-nitropyridine

HRID 473403

Reaktionsgleichung

Reaktionsgleichung von HRID 473403
[N+:1]([C:4]1[C:5]([CH:10]=[O:11])=[N:6][CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].CC1C=CC(S(O)(=O)=O)=CC=1.[CH2:23](O)[CH2:24][OH:25].O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[O:11]1[CH2:23][CH2:24][O:25][CH:10]1[C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=[CH:7][N:6]=1

Komponenten

7

Edukt 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 3293613-Nitropicolinaldehyde

Produkt 1

HCID 3293622-(1,3-Dioxolan-2-yl)-3-nitropyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

3-Nitro-2-pyridinecarbaldehyde (22 g, 144.74 mmol) was dissolved in toluene (500 mL). To the mixture was added catalytic amount of p-TSA (2 g) and ethylene glycol (40 mL) and the reaction flask equipped with Dean-Stark assembly was refluxed for 12 h at 120° C. After the reaction was complete, the reaction mixture was treated with water and ethyl acetate. The organic layer was separated and the aqueous layer was back extracted with ethyl acetate. The organic layers were combined and dried over anhydrous Na2SO4 and concentrated under reduced pressure to give a thick oily mass. The oily mass was then purified by silica gel column chromatography using 20% of ethyl acetate and hexane as eluent to give 2-(1,3-dioxolan-2-yl)-3-nitropyridine: 1H-NMR (CDCl3) δ: 4.2 (d, 5H), 6.5 (s, 1H), 7.5 (m, 1H), 8.3 (d, 1H), 8.9 (brs, 1H).

Aufarbeitung

  1. customthe reaction flask equipped with Dean-Stark
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was back extracted with ethyl acetate
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto give a thick oily mass
  7. customThe oily mass was then purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0e6942b0b24047c6b74d017462bca360
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633313B2

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