Imidazole → HCID 19045277、化合物

反応式

Cl[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([OH:12])=[C:7]([C:9](=[O:11])[CH3:10])[CH:8]=1.CN(C)C=O.[Na].[NH:19]1[CH:23]=[CH:22][N:21]=[CH:20]1>>[C:9]([C:7]1[CH:8]=[C:3]([CH2:2][N:19]2[CH:23]=[CH:22][N:21]=[CH:20]2)[CH:4]=[CH:5][C:6]=1[OH:12])(=[O:11])[CH3:10]

参加物

反応物 3

HCID 795Imidazole

HCID 225570132-Acetyl-4-chloromethyl phenol

HCID 86746767Sodium dimethylformamide

生成物 1

HCID 19045277HCID 19045277、化合物収率 33%

実験手順

To a mixture of 5'-(chloromethyl)-2'-hydroxyacetophenone (1.85 g, 10.0 mmol), sodium dimethylformamide was added imidazole (0.75 g, 11.0 mmol). The mixture was stirred four hours and concentrated in vacuo. The residue was stirred under 50 mL ethanol, filtered, and the filtrate concentrated in vacuo to give a residue. The residue was stirred under 30 mL chloroform, filtered, and the filtrate concentrated in vacuo to give crude product. The crude product was purified by flash chromatography eluting with 5:95 methanol:chloroform to give a solid. The solid was recrystallized from n-butlychloride to give 0.71 g (33%) product as a yellow crystalline solid, mp 106°-107° C.