반응 #6338

반응 방정식

diethyl 2-acetoxyethoxymethylphosphonate

sodium ethoxide

→

title compound

수율 70.0%

Diethyl 2-hydroxyethoxymethylphosphonate

수율 70.0%

용매

ethanol

반응 조건

후처리

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

실험 절차

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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