Реакция #6338

Уравнение реакции

diethyl 2-acetoxyethoxymethylphosphonate

sodium ethoxide

→

title compound

Выход 70.0%

Diethyl 2-hydroxyethoxymethylphosphonate

Выход 70.0%

Растворители

ethanol

Условия реакции

Обработка

1. 1
   ФильтрацияThe solution was filtered immediately
2. 2
   Промывкаthe resin washed with ethanol
3. 3
   Другоеthe combined filtrates evaporated under reduced pressure
4. 4
   ДругоеThe residue was chromatographed on silica gel (eluted with chloroform: methanol, 98:2)

Методика

To a solution of diethyl 2-acetoxyethoxymethylphosphonate* (16 g, 63 mmol) in absolute ethanol (150 ml), was added 0.5M sodium ethoxide (12.19 ml). After standing at ambient temperature overnight, 1R-120H resin was added until pH 6.5 was reached. The solution was filtered immediately, the resin washed with ethanol and the combined filtrates evaporated under reduced pressure. The residue was chromatographed on silica gel (eluted with chloroform: methanol, 98:2) to yield the title compound as a colourless oil (9.3g, 70%). IR: νmax (film) 3420, 3000, 1450, 1395, 1240, 1170, 1130, 1030, 970 cm-1. 1H NMR: δH (CDCl3) 1.35 (6H,t,J=7Hz, (OCH2CH3)2), 3.75 (4H,br.s, OCH2CH2O), 3.90 (2H,d,J=8Hz, O--CH2P), 4.20 (4H,m,(O--CH2CH3)2), 5.20 (1H,br.s, D 2 O exchangeable, OH). Found: C,38.64; H,8.27%. C7H17PO5.0.3H2O requires: C,38.63; H,8.01%.

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