Reacción #5609

Ecuación de reacción

5-benzyloxy-2-chloromethyl-4-pyridone

triphenylphosphine

ethyl acetate

→

5-benzyloxy-2-vinyl-4-pyridone

Rendimiento 66.2%

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónThe precipitate was collected by filtration
2. 2
   Lavadowashed with ethyl acetate
3. 3
   workup.DISSOLUTIONdissolved in dichloromethane (500 ml)
4. 4
   workup.ADDITIONTo the solution were added water (300 ml) and 38% aqueous formaldehyde (100 ml)
5. 5
   Otrothe organic layer was separated
6. 6
   Lavadowashed with water
7. 7
   Secadodried over magnesium sulfate
8. 8
   Concentraciónconcentrated under reduced pressure
9. 9
   OtroThe product was isolated by column chromatography on silica gel with ethyl acetate as an eluent

Procedimiento

A solution of 5-benzyloxy-2-chloromethyl-4-pyridone (10.0 g) and triphenylphosphine (10.5 g) in N,N-dimethylformamide (50 ml) was stirred for 5 hours at 90°-100° C. The resulting mixture was poured into ethyl acetate (800 ml). The precipitate was collected by filtration, washed with ethyl acetate and dissolved in dichloromethane (500 ml). To the solution were added water (300 ml) and 38% aqueous formaldehyde (100 ml). The mixture was adjusted to pH 10-10.5 with potassium carbonate. After being stirred for 3 hours at 35°-40° C., the organic layer was separated, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The product was isolated by column chromatography on silica gel with ethyl acetate as an eluent to give 5-benzyloxy-2-vinyl-4-pyridone (6.02 g).

Fuente