Reacción #1951060

Ecuación de reacción

Bromomethyl-cyclopropane

triisopropyl phosphite

→

cyclopropylmethyl-phosphonic acid diisopropyl ester

Rendimiento 94.3%

Disolventes

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaheated
2. 2
   Temperaturato cool to ambient temperature
3. 3
   LavadoThe solution was washed with saturated sodium bicarbonate (350 mL)
4. 4
   SecadoThe organic phase was dried with magnesium sulfate
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated by rotary evaporation

Procedimiento

Bromomethyl-cyclopropane (26.00 g, 0.193 mol) was added to triisopropyl phosphite (35.9 mL, 0.30 mol) at ambient temperature, under a nitrogen atmosphere. The resulting solution was stirred and heated at reflux (144° C. bath temperature) overnight. The reaction mixture was allowed to cool to ambient temperature and then ethyl acetate (350 mL) was added. The solution was washed with saturated sodium bicarbonate (350 mL) and then with saturated brine (2×350 mL). The organic phase was dried with magnesium sulfate, filtered, and concentrated by rotary evaporation and then under high vacuum to yield 39.96 g of cyclopropylmethyl-phosphonic acid diisopropyl ester (0.182 mol, 94% yield) as a colorless oil. 1H NMR (400 MHz, DMSO) δ 4.63-4.54 (m, 2H); 1.67-1.60 (d of d, 2H) 1.27-1.24 (d of d, 12H); 0.85-0.75 (m, 1H); 0.52-0.46 (m, 2H); 0.21-0.16 (m, 2H); ESMS (m/z): M+1)+ found, 221; (M+23)+ found, 243.

Fuente