反応 #47203

反応方程式

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

収率 34.0%

溶媒

methanol

反応条件

後処理

1. 1
   workup.ADDITIONAfter the addition
2. 2
   その他the solvent was removed under vacuum
3. 3
   workup.DISSOLUTIONthe crude product was dissolved in water
4. 4
   抽出extracted with ethyl acetate
5. 5
   洗浄The combined organic layers was washed with brine
6. 6
   その他dried
7. 7
   その他the solvent removed under vacuum
8. 8
   その他The crude product was purified by column chromatography (silicagel, dichloromethane:methanol 95:5)

実験手順

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.

出典