反応 #93366

反応方程式

sodium hydride

2-methylbenzimidazole

4-(3-tolyloxy)benzyl bromide

water

→

2-methyl-1-[4-(3-tolyloxy)benzyl]benzimidazole

収率 71.1%

溶媒

dimethylformamide

dimethylformamide

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGstirring
3. 3
   workup.WAITin 30 minutes
4. 4
   workup.STIRRINGby stirring at room temperature overnight
5. 5
   その他After completion of the reaction
6. 6
   抽出extracted with toluene (30 ml) two times
7. 7
   洗浄The toluene layer was washed with water
8. 8
   乾燥dried over anhydrous sodium sulfate
9. 9
   workup.DISTILLATIONdistilled under reduced pressure
10. 10
    その他to remove toluene
11. 11
    その他The residue was purified by silica gel column chromatography

実験手順

To a suspension of sodium hydride (0.14 g, 3.6 mmole; 62% in oil) in anhydrous dimethylformamide (10 ml), 2-methylbenzimidazole (0.48 g, 3.6 mmole) was added while stirring, and stirring was continued at room temperature for 1 hour. The resultant mixture was cooled to 5°-10° C., and a solution of 4-(3-tolyloxy)benzyl bromide (1.00 g, 3.6 mmole) in anhydrous dimethylformamide (5 ml) was dropwise added thereto in 30 minutes, followed by stirring at room temperature overnight. After completion of the reaction, the reaction mixture was poured into water (100 ml) and extracted with toluene (30 ml) two times. The toluene layer was washed with water, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove toluene. The residue was purified by silica gel column chromatography to give 2-methyl-1-[4-(3-tolyloxy)benzyl]benzimidazole (0.84 g) as colorless liquid. nD27.0 1.6112.

出典