Reacción #1951059

Ecuación de reacción

Divinyl-(4-Fluorophenylmethyl)-phosphine oxide

benzylamine

benzylamine

→

1-benzyl-4-(4-fluorophenylmethyl)-[1,4]azaphosphinane 4-oxide

Rendimiento 77.5%

Disolventes

THF

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe reaction mixture was heated for an additional six hours at 90° C
2. 2
   ConcentraciónThe reaction mixture was concentrated by rotary evaporation
3. 3
   Extracciónthe product was extracted into dichloromethane
4. 4
   Lavadowashed with saturated brine
5. 5
   SecadoThe organic phase was dried with sodium sulfate
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated by rotary evaporation
8. 8
   LavadoThe product was then eluted from the silica with a solution of 10% methanol in ethyl acetate
9. 9
   OtroThe solvents were removed by rotary evaporation

Procedimiento

Divinyl-(4-Fluorophenylmethyl)-phosphine oxide (0.719 g, 3.42 mmol) and benzylamine (0.45 mL, 4.11 mmol) were dissolved in a mixture of THF (15 mL) and deionized water (15 mL). The reaction mixture was heated at 82° C. for 22 hours. The reaction was not complete and so an additional 0.04 mL of benzylamine was added and the reaction mixture was heated for an additional six hours at 90° C. The reaction mixture was concentrated by rotary evaporation and the product was extracted into dichloromethane and washed with saturated brine. The organic phase was dried with sodium sulfate, filtered, and concentrated by rotary evaporation. The crude product was taken up in 1:1 ethyl acetate:dichloromethane and passed through a plug of silica. The product was then eluted from the silica with a solution of 10% methanol in ethyl acetate. The solvents were removed by rotary evaporation to yield 0.84 g of 1-benzyl-4-(4-fluorophenylmethyl)-[1,4]azaphosphinane 4-oxide (2.65 mmol, 77%). 1H NMR (400 MHz, CDCl3) δ 7.34-7.25 (m, 5H); 7.25-7.20 (m, 2H); 7.04-6.98. (m, 2H); 3.6 (s, 2H); 3.17-3.12 (d, 2H); 3.00-2.85 (m, 2H); 2.81-2.66 (m, 2H); 1.98-1.75 (m, 4H).

Fuente