Reacción #65150

Ecuación de reacción

Water

chlorosulfonyl isocyanate

cis-methyl hydrogen cyclopropane-1,2-dicarboxylate

DMF

→

methyl cis-2-cyanocyclopropanecarboxylate

Rendimiento 55.8%

Disolventes

benzene

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrohad been synthesized by the process of Journal of Organic Chemistry, Vol. 36
2. 2
   TemperaturaAfter cooling
3. 3
   workup.STIRRINGby stirring for 30 minutes
4. 4
   Extracciónthe reaction mixture was extracted with benzene
5. 5
   LavadoThe organic layer was washed successively with water
6. 6
   Secadoa saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate
7. 7
   OtroThe solvent was removed by distillation under reduced pressure
8. 8
   workup.DISTILLATIONthe residue was distilled under reduced pressure

Procedimiento

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.

Fuente