تفاعل #66768

معادلة التفاعل

HCl

1-cyclopropyl-1H-pyrrole-2-carbaldehyde

diethyl succinate

KOAc

→

Ethyl 4-acetoxy-1-cyclopropyl-1H-indole-6-carboxylate

المذيبات

acetic anhydride

EtOH

EtOH

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe mixture was refluxed overnight
2. 2
   أخرىEtOH was evaporated
3. 3
   استخلاصThe residue was extracted with CHCl3
4. 4
   تجفيفthe organic layer was dried over Na2SO4
5. 5
   تركيزconcentrated
6. 6
   أخرىto give red oil
7. 7
   درجة الحرارةThe mixture was refluxed for 30 min.
8. 8
   درجة الحرارةto cool to room temperature
9. 9
   ترشيحThe mixture was filtrated
10. 10
    تركيزthe filtrate was concentrated
11. 11
    أخرىThe residue was purified by silicagel column chromatography (hexane/EtOAc)
12. 12
    أخرىto give

الإجراء التجريبي

Na (14.6 g) was added portion wise to EtOH (400 ml) with stirring at room temperature. To the mixture was added a solution of 1-cyclopropyl-1H-pyrrole-2-carbaldehyde (38.9 g) and diethyl succinate (48.2 ml) in EtOH (100 ml) at 50° C., then the mixture was refluxed overnight. 140 ml of aqueous 5N HCl was added to the mixture at 0° C. and EtOH was evaporated. The residue was extracted with CHCl3, the organic layer was dried over Na2SO4 and concentrated to give red oil. The material was dissolved in 400 ml of acetic anhydride and KOAc (47.4 g) was added thereto. The mixture was refluxed for 30 min. and allowed to cool to room temperature. The mixture was filtrated and the filtrate was concentrated. The residue was purified by silicagel column chromatography (hexane/EtOAc) to give intended compound a red oil.

المصدر