N-Methoxy-N-methylnicotinamide → 1-(Pyridin-3-yl)butan-1-one

HRID 593508

Reaktionsgleichung

Reaktionsgleichung von HRID 593508
CN(OC)[C:3](=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][CH:5]=1.[CH2:13]([Mg]Cl)[CH2:14][CH3:15]>C1COCC1>[N:6]1[CH:7]=[CH:8][CH:9]=[C:4]([C:3](=[O:10])[CH2:13][CH2:14][CH3:15])[CH:5]=1

Komponenten

4

Edukt 2

HCID 10558996N-Methoxy-N-methylnicotinamideHCID 178455855HCID 178455855, Verbindung

Produkt 1

HCID 4595021-(Pyridin-3-yl)butan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A flask is charged with N-methyl-N-methoxy-nicotinamide (1.0 g, 6.02 mmol) and THF (10 mL). Propyl magnesium chloride (2M in THF, 3.31 mL, 6.62 mmol) is added and the mixture is stirred at room temperature overnight. It is quenched with saturated sodium bicarbonate solution and extracted with dichloromethane. The combined organic layer is dried over sodium sulfate and concentrated in vacuo to afford 1-pyridin-3-yl-butan-1-one as a yellow oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.03 (t, J=7.5 Hz, 3H), 1.74-1.87 (m, 2H), 2.97 (t, J=7.3 Hz, 2H), 7.42 (dd, J=8.0, 4.9 Hz, 1H), 8.24 (dt, J=8.0, 2.0, 1.9 Hz, 1H), 8.78 (dd, J=4.9, 2.0 Hz, 1H), 9.18 (d, J=2.0 Hz, 1H).

Aufarbeitung

  1. customIt is quenched with saturated sodium bicarbonate solution
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic layer is dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-cfa4693cea0846d4b7f33ec55788eace
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242963B2

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