Reacción #79345

Ecuación de reacción

dibromobutane

methyl 2-cyanoacetate

DBU

→

desired product

Rendimiento 58.0%

methyl 1-cyanocyclopentanecarboxylate

Rendimiento 58.0%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe internal temperature increased to 70° C. during the addition
2. 2
   Temperaturato cool to rt
3. 3
   Otrobefore quenching with H2O (800 mL)
4. 4
   ExtracciónThe product was extracted with Et2O (3×300 mL)
5. 5
   LavadoThe ether layer was washed with 1N HCl (400 mL) and H2O (400 mL)
6. 6
   SecadoThe combined extracts were dried over magnesium sulfate
7. 7
   Concentraciónconcentrated to a crude oil that
8. 8
   workup.DISTILLATIONwas distilled under high vacuum at 80° C.

Procedimiento

A solution of methyl 2-cyanoacetate (30 mL, 340 mmol) in DMF (26 mL) and DBU (112 mL, 748 mmol) was heated to 50° C. for 15 min and then cooled to −20° C. To this stirred solution was added dibromobutane 18. The internal temperature increased to 70° C. during the addition. The reaction was set aside to cool to rt before quenching with H2O (800 mL). The product was extracted with Et2O (3×300 mL). The ether layer was washed with 1N HCl (400 mL) and H2O (400 mL). The combined extracts were dried over magnesium sulfate, and concentrated to a crude oil that was distilled under high vacuum at 80° C. to yield the desired product in 58% yield.

Fuente