Реакция #49894

Уравнение реакции

aldehyde

3,5-di-tert-butyl-4-methoxybenzaldehyde

3-phenylpropylamine

THF

diethylphosphite

→

yellow oil

Выход 37.0%

Diethyl α-(3.5-di-tert-butyl-4-methoxyphenyl)-N-(3-phenylpropyl)-aminomethylphosphonate

Выход 37.0%

Условия реакции

Обработка

1. 1
   Температураthe resulting mixture heated at i10° C
2. 2
   ДругоеPurification by column chromatography

Методика

This aldehyde was reacted with 0.63 g (4.68 mmol) 3-phenylpropylamine in 25 ml THF, then 0.65 g (4.68 mmol) diethylphosphite was added and the resulting mixture heated at i10° C. for 4 h. Purification by column chromatography gave 0.9 g (37% of a yellow oil). IR (film) 3400 cm-1 (broad): NH, 1440: tert-Bu, 1220: P=O, 1020: P--O--C. NMR (CDCl3): δ=7.24 and 7.14 (2 m, 5H) phenyl H 7.26 (d, JP-H =2 Hz, 2H): aromatic H, 3,5 di-tert-butyl-4-hydroxyphenyl 4.05, 3.93 and 3.79 (3 m, 4H): P--O--CH2 --CH3 3.95 (d, JP-H =19 Hz, 1H): CH--PO3ET2 3.66 (s, 3H): Ph--O--CH3 2.66 and 2.59 (2 m, 4H): NH--CH2 --CH2 --CH2 --Ph 1.79 (m, 3H): NH and NH--CH2 --CH2 --CH2 --Ph 1.42 (s, 18H): tert-Bu 1.27 and 1.10 (2t, J=7 Hz, 6H): P--O--CH2 --CH3MS: m/e=504: M+ +366:M+ --PO3Et2

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