HCID 19993539, compound → HCID 19993529, compound

Participants

Reaction Steps

10% Palladium on charcoal (4.5 g) was added to a solution of diethyl 3-benzyloxypropoxymethylphosphonate (14.6 g, 46 mmol) in ethanol (250 ml) and 5M hydrochloric acid (4 ml) and the reaction stirred under an atmosphere of hydrogen for 6 h. The catalyst was removed by filtration through a glass-fibre paper and the ethanol evaporated under reduced pressure. The residue was then dissolved in chloroform, dried (MgSO4), filtered and reduced in vacuo to give diethyl 3-hydroxypropoxymethylphosphonate as a colourless oil (8.97 g, 86%); νmax (film) 3419, 2935, 1241, 1029 cm-1); δH (CDCl3) 1.46(6H, t, J7.1 Hz, (CH3CH2O)2), 83(2H, m, CH2CH2CH2), 3.73-3.79(5H, m, CH2CH2CH2 and OH (D2O exchangeable)), 3.81(2H, d, J7.9 Hz, CH2P), 4.18(4 H, m, (CH3CH2O)2).

Provenance & Evidence