反应 #1951059

反应方程式

Divinyl-(4-Fluorophenylmethyl)-phosphine oxide

benzylamine

benzylamine

→

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

收率 77.5%

溶剂

THF

water

反应条件

后处理

1. 1
   温度the reaction mixture was heated for an additional six hours at 90° C
2. 2
   浓缩The reaction mixture was concentrated by rotary evaporation
3. 3
   萃取the product was extracted into dichloromethane
4. 4
   洗涤washed with saturated brine
5. 5
   干燥The organic phase was dried with sodium sulfate
6. 6
   过滤filtered
7. 7
   浓缩concentrated by rotary evaporation
8. 8
   洗涤The product was then eluted from the silica with a solution of 10% methanol in ethyl acetate
9. 9
   其他The solvents were removed by rotary evaporation

实验过程

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).

来源