反应 #6338

反应方程式

diethyl 2-acetoxyethoxymethylphosphonate

sodium ethoxide

→

title compound

收率 70.0%

Diethyl 2-hydroxyethoxymethylphosphonate

收率 70.0%

溶剂

ethanol

反应条件

后处理

1. 1
   过滤The solution was filtered immediately
2. 2
   洗涤the resin washed with ethanol
3. 3
   其他the combined filtrates evaporated under reduced pressure
4. 4
   其他The residue was chromatographed on silica gel (eluted with chloroform: methanol, 98:2)

实验过程

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%.

来源