반응 #1951059

반응 방정식

Divinyl-(4-Fluorophenylmethyl)-phosphine oxide

benzylamine

benzylamine

→

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

수율 77.5%

용매

THF

water

반응 조건

후처리

1. 1
   온도the reaction mixture was heated for an additional six hours at 90° C
2. 2
   농축The reaction mixture was concentrated by rotary evaporation
3. 3
   추출the product was extracted into dichloromethane
4. 4
   세척washed with saturated brine
5. 5
   건조The organic phase was dried with sodium sulfate
6. 6
   여과filtered
7. 7
   농축concentrated by rotary evaporation
8. 8
   세척The product was then eluted from the silica with a solution of 10% methanol in ethyl acetate
9. 9
   기타The solvents were removed by rotary evaporation

실험 절차

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).

출처