Sodium ethoxide → Diethyl 2-hydroxyethoxymethanephosphonate

HRID 6242

Reaction equation

HRID 6242 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

HCID 10262588Diethyl 2-hydroxyethoxymethanephosphonateYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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%.

Workup

  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)

Sources & evidence

ORD record
ord-86fb1dcff3c742f79157360a3f708f8a
Source dataset
uspto-grants-1993_09
Patent number
US05247085

Linked notes

Loading…