Reacción #2068

Ecuación de reacción

N-butyl-2-chloroacetamide

potassium iodide

sodium chloride

Tetraethyl methylenebisphosphonate

sodium hydride

hydride

→

title compound

Rendimiento 70.0%

N-butyl-3,3-bis(diethoxyphosphinyl)propionamide

Rendimiento 70.0%

Disolventes

THF

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas consumed
2. 2
   Otroprecipitated
3. 3
   workup.ADDITIONAdditional sodium hydride (20 mg) was added
4. 4
   Temperaturathe reaction mixture was heated an additional 4 hours
5. 5
   TemperaturaAfter cooling
6. 6
   workup.ADDITIONthe mixture was poured into 1N HCl (10 mL) and diethyl ether (50 mL)
7. 7
   workup.ADDITIONwas added
8. 8
   ExtracciónThe diethyl ether layer was further extracted with water (3×10 mL)
9. 9
   ExtracciónThe combined aqueous fractions were extracted with dichloromethane (4×25 mL)
10. 10
    SecadoThe combined extracts were dried (Na2SO4)
11. 11
    Concentraciónconcentrated

Procedimiento

Tetraethyl methylenebisphosphonate (1.44 g, 5.0 mmol) in THF (1 mL) was added to a slurry of 80% sodium hydride (150 mg, 5.0 mmol) in THF (4 mL) at 0° C. The reaction was warmed to room temperature and stirred until all of the hydride was consumed. A solution of N-butyl-2-chloroacetamide (0.75 g, 5.0 mmol) in THF (1 ml) and potassium iodide (100 mg) were then added. The reaction mixture was then heated at 50° C. for 18 hours, during which time sodium chloride precipitated. Additional sodium hydride (20 mg) was added, and the reaction mixture was heated an additional 4 hours. After cooling, the mixture was poured into 1N HCl (10 mL) and diethyl ether (50 mL) was added. The diethyl ether layer was further extracted with water (3×10 mL). The combined aqueous fractions were extracted with dichloromethane (4×25 mL). The combined extracts were dried (Na2SO4) and concentrated to give the title compound (1.40 g, 70%) as an oil.

Fuente