تفاعل #47203

معادلة التفاعل

sodium methoxide

1-cyano-3,3-dimethylbut-1-en-2-yl 4-methylbenzenesulfonate

diethyl aminomalonate hydrochloride salt

→

methyl 3-amino-5-tert-butyl-1H-pyrrole-2-carboxylate

المردود 34.0%

المذيبات

methanol

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONAfter the addition
2. 2
   أخرىthe solvent was removed under vacuum
3. 3
   workup.DISSOLUTIONthe crude product was dissolved in water
4. 4
   استخلاصextracted with ethyl acetate
5. 5
   غسيلThe combined organic layers was washed with brine
6. 6
   أخرىdried
7. 7
   أخرىthe solvent removed under vacuum
8. 8
   أخرىThe crude product was purified by column chromatography (silicagel, dichloromethane:methanol 95:5)

الإجراء التجريبي

To a stirred sodium methoxide solution (15% by weight, 80 mL total) was added drop-wise a solution of 1-cyano-3,3-dimethylbut-1-en-2-yl 4-methylbenzenesulfonate (10.0 g, 36 mmol) and diethyl aminomalonate hydrochloride salt (9.0 g, 43 mmol) in methanol (50 mL). After the addition was completed, the reaction was stirred at room temperature for 2 hours, the solvent was removed under vacuum and the crude product was dissolved in water and extracted with ethyl acetate. The combined organic layers was washed with brine, dried and the solvent removed under vacuum. The crude product was purified by column chromatography (silicagel, dichloromethane:methanol 95:5) to afford 2.4 g of the desired methyl 3-amino-5-tert-butyl-1H-pyrrole-2-carboxylate used as such in the next step.

المصدر