Sodium ethoxide → Diethyl 2-hydroxyethoxymethanephosphonate

HRID 6242

Reaktionsgleichung

Reaktionsgleichung von HRID 6242
C([O:4][CH2:5][CH2:6][O:7][CH2:8][P:9](=[O:16])([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])(=O)C.[O-]CC.[Na+]>C(O)C>[OH:4][CH2:5][CH2:6][O:7][CH2:8][P:9](=[O:16])([O:10][CH2:11][CH3:12])[O:13][CH2:14][CH3:15]

Komponenten

4

Edukt 2

HCID 2723922Sodium ethoxideHCID 139159842-((Diethoxyphosphoryl)methoxy)ethyl acetate

Produkt 1

HCID 10262588Diethyl 2-hydroxyethoxymethanephosphonateAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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%.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-86fb1dcff3c742f79157360a3f708f8a
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05247085

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