反応 #5609

反応方程式

5-benzyloxy-2-chloromethyl-4-pyridone

triphenylphosphine

ethyl acetate

→

5-benzyloxy-2-vinyl-4-pyridone

収率 66.2%

溶媒

N,N-dimethylformamide

反応条件

後処理

1. 1
   ろ過The precipitate was collected by filtration
2. 2
   洗浄washed 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
   その他the organic layer was separated
6. 6
   洗浄washed with water
7. 7
   乾燥dried over magnesium sulfate
8. 8
   濃縮concentrated under reduced pressure
9. 9
   その他The product was isolated by column chromatography on silica gel with ethyl acetate as an eluent

実験手順

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).

出典