反应 #1951063

反应方程式

divinyl-phosphine oxide

benzylamine

THF

benzylamine

→

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

收率 81.0%

溶剂

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 ethanol
9. 9
   其他The solvents were removed by rotary evaporation

实验过程

Cyclopropylmethyl)-divinyl-phosphine oxide (3.56, 22.8 mmol) and benzylamine (3.0 mL, 27.4 mmol) were dissolved in a mixture of THF (100 mL) and deionized water (100 mL). The reaction mixture was heated at 90° C. for 24 hours. The reaction was not complete and so additional benzylamine (1.0 mL, 9.1 mmol) 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 ethyl acetate and passed through a plug of silica. The product was then eluted from the silica with ethanol. The solvents were removed by rotary evaporation to yield 4.835 g of 1-benzyl-4-(cyclopropylmethyl)-[1,4]azaphosphinane 4-oxide (18.38 mmol, 81%) as an off-white crystalline solid. 1H NMR (400 MHz, DMSO) δ 7.38-7.30 (m, 4H); 7.30-7.24 (m, 1H); 3.59 (s, 2H); 2.81-2.63 (m, 4H); 1.94-1.83 (m, 2H); 1.82-1.71 (m, 2H); 1.74-1.68 (d of d, 2H); 0.96-0.83 (m, 1H); 0.56-0.49 (m, 2H); 0.22-0.14 (m, 2H); ESMS (m/z): (M+1)+ found, 264; (M+23)+ found, 286.

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