تفاعل #410364

معادلة التفاعل

2-chloro-1H-benzimidazole

tetrahydrofuran

2-chloroethyl ethyl ether

potassium bis(trimethylsilyl)amide

→

1-(2-ethoxyethyl)-2-chloro-1H-benzimidazole

المذيبات

water

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONAdd dropwise
2. 2
   درجة الحرارةWarm to ambient temperature
3. 3
   درجة الحرارةheat to reflux
4. 4
   workup.WAITAfter 12 hours
5. 5
   درجة الحرارةcool to ambient temperature
6. 6
   أخرىSeparate the organic layer
7. 7
   استخلاصextract the aqueous layer with dichloromethane
8. 8
   تجفيفDry the combined organic layers over Na2SO4
9. 9
   ترشيحfilter
10. 10
    أخرىevaporate in vacuo

الإجراء التجريبي

Combine 2-chloro-1H-benzimidazole (15.3 g, 100 mmol) and tetrahydrofuran (300 mL). Cool to −70° C. Add dropwise, a solution of potassium bis(trimethylsilyl)amide (200 mL, 0.5 M in toluene, 100 mmol). After 30 minutes, add 2-chloroethyl ethyl ether (22.2 g, 200 mmol) and tetrabutylammonium bromide (0.5 g). Warm to ambient temperature and heat to reflux. After 12 hours, cool to ambient temperature and add water. Separate the organic layer and extract the aqueous layer with dichloromethane. Dry the combined organic layers over Na2SO4, filter, and evaporate in vacuo to give 1-(2-ethoxyethyl)-2-chloro-1H-benzimidazole.

المصدر