3-Pyridinepropanol → 3-(Pyridin-3-yl)propanal

HRID 1186391

Reaktionsgleichung

Reaktionsgleichung von HRID 1186391
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][OH:10])[CH:2]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH:9]=[O:10])[CH:2]=1

Komponenten

4

Edukt 2

HCID 178613-PyridinepropanolHCID 159087Triacetoxyperiodinane

Produkt 1

HCID 111054123-(Pyridin-3-yl)propanalAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-Pyridinepropanol (300 mg, 2.2 mmol) was dissolved in dichloromethane (5 mL). To this, the Dess-Martin reagent (1.0 g) was added with cooling in an ice bath and the mixture was stirred at the same temperature for 2 hours and successively at room temperature for 3 hours. The solvent in the reaction mixture was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/methanol=1/0 to 10/1) to give 3-(pyridin-3-yl)propanal (180 mg, yield: 61%).

Aufarbeitung

  1. temperaturewith cooling in an ice bath
  2. customThe solvent in the reaction mixture was evaporated off under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (chloroform/methanol=1/0 to 10/1)

Quellen und Nachweise

ORD-Eintrag
ord-d0c2e372d0714bb590a9d46cd7f14c27
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673908B2

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