反応 #65150

反応方程式

Water

chlorosulfonyl isocyanate

cis-methyl hydrogen cyclopropane-1,2-dicarboxylate

DMF

→

methyl cis-2-cyanocyclopropanecarboxylate

収率 55.8%

溶媒

benzene

反応条件

後処理

1. 1
   その他had been synthesized by the process of Journal of Organic Chemistry, Vol. 36
2. 2
   温度After cooling
3. 3
   workup.STIRRINGby stirring for 30 minutes
4. 4
   抽出the reaction mixture was extracted with benzene
5. 5
   洗浄The organic layer was washed successively with water
6. 6
   乾燥a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate
7. 7
   その他The solvent was removed by distillation under reduced pressure
8. 8
   workup.DISTILLATIONthe residue was distilled under reduced pressure

実験手順

In 25 ml of benzene was dissolved 13.77 g (97 mmol) of chlorosulfonyl isocyanate, and to the solution was added 12.7 g (88 mmol) of cis-methyl hydrogen cyclopropane-1,2-dicarboxylate which had been synthesized by the process of Journal of Organic Chemistry, Vol. 36, pp. 3356-3361 (1971). The mixture was stirred on an oil bath at 60° C. for 30 minutes. After cooling, 13.6 ml (176 mmol) of DMF was added thereto, followed by stirring for 30 minutes. Water was added thereto, and the reaction mixture was extracted with benzene. The organic layer was washed successively with water and a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, and the residue was distilled under reduced pressure to obtain 6.14 g (55.7%) of methyl cis-2-cyanocyclopropanecarboxylate.

出典