Reacción #51108

Ecuación de reacción

Hydrazine

methyl 4-pentylbicyclo[2.2.2]octane-1-carboxylate

water

→

4-pentylbicyclo[2.2.2]octane-1-carbohydrazide

Disolventes

ethylene glycol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaunder reflux for 17 h
2. 2
   Extracciónextracted with methylene chloride (3×600 mL)
3. 3
   LavadoThe combined extracts were washed twice with water, brine
4. 4
   Secadodried (MgSO4)
5. 5
   Concentraciónconcentrated in vacuo

Procedimiento

Hydrazine (anhydrous, 103 mL, 88.7 mmol) was added to a solution of methyl 4-pentylbicyclo[2.2.2]octane-1-carboxylate (2-B) in ethylene glycol (180 mL) and the mixture was stirred under reflux for 17 h. After cooling to room temperature, the mixture was poured into water (1500 mL) and extracted with methylene chloride (3×600 mL). The combined extracts were washed twice with water, brine, dried (MgSO4) and concentrated in vacuo to provide 4-pentylbicyclo[2.2.2]octane-1-carbohydrazide (2-C). 1H NMR (500 MHz, CDCl3): δ 0.90 (t, 3H); 1.21 (m, 8H); 1.43 (m, 6H); 1.74 (m, 6H); 3.85 (broad s, 2H); 6.81 (broad s, 1H) ppm.

Fuente