Ethyl Acetate → 5-Chloro-2-(3-methoxypropyl)pyridine-4-carbaldehyde

HRID 2428092Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2428092
[Cl:1][C:2]1[C:3]([CH:13](OC)[O:14]C)=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][O:11][CH3:12])=[N:6][CH:7]=1.CCOC(C)=O.[OH-].[Na+]>Cl>[Cl:1][C:2]1[C:3]([CH:13]=[O:14])=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][O:11][CH3:12])=[N:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 667628875-Chloro-4-(dimethoxymethyl)-2-(3-methoxypropyl)pyridine

Produkt 1

HCID 714237335-Chloro-2-(3-methoxypropyl)pyridine-4-carbaldehydeAusbeute 99,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

5-Chloro-4-dimethoxymethyl-2-(3-methoxy-propyl)-pyridine (25.5 g, 98.2 mmol) was dissolved in aq. 1M HCl (500 mL), and the mixture was heated to 80° C. for 2 h. The mixture was allowed to cool to rt, and EtOAc was added. The mixture was cooled to 0° C., and was basified with aq. 2.5M NaOH to pH=10. The layers were separated, and the org. layer was dried over MgSO4, filtered, and concentrated under reduced pressure. Drying the residue under high vacuum yielded the crude title compound (98.1 mmol, 99%) that was used further without purification. LC-MS: tR=0.62 min; ES+: 246.12.

Aufarbeitung

  1. temperatureto cool to rt
  2. temperatureThe mixture was cooled to 0° C.
  3. customThe layers were separated
  4. dry with materiallayer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customDrying the residue under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-f30bcd5c19084a86a7401744f0f9ac7e
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07968720B2

Notizen zur Reaktion

Wird geladen…