Reaktion #8621

Reaktionsgleichung

HCl

allyl magnesium chloride

4-methoxypyridine

benzyl chloroformate

→

desired product

N-Cbz-6-allyl-2,3-dihydro-1H-pyridin-4-one

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthen cooled to −75° C.
2. 2
   workup.WAITThe solution is held at −75° C. for 4 hours
3. 3
   workup.ADDITIONis added
4. 4
   Sonstigeto quench
5. 5
   Sonstigethe reaction
6. 6
   SonstigeThe organic layer is isolated
7. 7
   Sonstigepurified over silica gel

Vorschrift

To a solution of 4-methoxypyridine (50 mL, 0.492 mol) in toluene (1 L) is added benzyl chloroformate (70.3 mL, 0.492 mol) at 0° C. The resulting mixture is stirred at 0° C. for 30 minutes then cooled to −75° C. and allyl magnesium chloride (295.5 mL, 0.591 mol) is added. The solution is held at −75° C. for 4 hours and allowed to warm to 0° C. at which point a solution of 20% HCl is added to quench the reaction. The organic layer is isolated and purified over silica gel to yield the desired product.

Quelle