반응 #47203

반응 방정식

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

수율 34.0%

용매

methanol

반응 조건

후처리

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

실험 절차

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.

출처