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

HRID 561827Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 561827
[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 an aq. 2.5M NaOH until a pH=10 was reached. 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-14394d12fbf9447fbc12ce1a6ba901e2
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063105B2

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