Sulfolane → 1-(2-Naphthylmethyl)-2-acetyl-5-methylpyridinium bromide

反応式

[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][N:5]=1)(=[O:3])[CH3:2].[Br:11][CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=1.C1S(=O)(=O)CCC1>C(OCC)(=O)C>[Br-:11].[CH:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:21]=[CH:22][C:13]=1[CH2:12][N+:5]1[CH:6]=[C:7]([CH3:10])[CH:8]=[CH:9][C:4]=1[C:1](=[O:3])[CH3:2]

参加物

実験手順

Twenty-six grams (0.192 m) of 2-acetyl-5-methylpyridine and 40 g (0.181 m) of 2-bromomethylnaphthalene was added to 78 ml of tetramethylene-sulfone. After heating the mixture for two hours on a steam bath, the mixture was allowed to stand at room temperature for twenty days. The reaction mixture was diluted with 700 ml of ethyl acetate and product oiled out. This first portion of ethyl acetate was decanted and the gum was extracted with 3×100 ml portions of ether. A total of 58 g (85-90%) of gum remained and after storing in the cold for one week some solid formed; however no attempt was made to purify this material further.