反応 #1951059

反応方程式

Divinyl-(4-Fluorophenylmethyl)-phosphine oxide

benzylamine

benzylamine

→

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

収率 77.5%

溶媒

THF

water

反応条件

後処理

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

実験手順

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).

出典