反応 #74862

反応方程式

5-(3-bromophenyl)-1-methyl-3-phenyl-4(1H)-pyridinone

methyl methanesulfonate

pyridinone

→

5-(3-bromophenyl)-4-methoxy-1-methyl-3-phenylpyridinium methanesulfonate

溶媒

benzene

反応条件

後処理

1. 1
   workup.ADDITIONA mixture of 4.0 g
2. 2
   温度under reflux for 6 hours
3. 3
   温度The mixture was cooled
4. 4
   その他the solvent removed in vacuo
5. 5
   その他to crystallize
6. 6
   その他After the front-running spot was removed the column
7. 7
   その他was flushed with ethanol
8. 8
   その他removed
9. 9
   その他The column was flushed with ethanol
10. 10
    その他the ethanol removed
11. 11
    その他to yield 0.75 g

実験手順

A mixture of 4.0 g. of 5-(3-bromophenyl)-1-methyl-3-phenyl-4(1H)-pyridinone and 20 ml. of methyl methanesulfonate in benzene was heated under reflux for 6 hours. The mixture was cooled and the solvent removed in vacuo. The product failed to crystallize. The product was passed over a silica gel column in ethyl acetate. After the front-running spot was removed the column was flushed with ethanol. The ethanol fractions were again placed on a silica gel solumn and front-running impurities removed. The column was flushed with ethanol and the ethanol removed to yield 0.75 g. of a hard glass. The nmr spectrum of the product was consistent with the structure of the expected salt. For example, there was an N-CH3 peak at 4.4 ppm and a peak at 8.7 ppm attributed to the hydrogens at the 2- and 6-positions of the pyridine ring. As is characteristic of pyridinium salts, both these peaks were shifted from the corresponding peaks in the starting pyridinone.

出典