Réaction #6353

Équation de réaction

diethyl (S)-[2-benzyloxy-1-(t-butyldiphenylsilyloxymethyl)ethoxy]methylphosphonate

hydrogen

CH2Cl2 MeOH

→

title compound

Rendement 85.1%

Diethyl (S)-[1-(t-butyldiphenylsilyloxymethyl)-2-hydroxyethoxy]methylphosphonate

Rendement 85.1%

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   FiltrationThe reaction mixture was filtered
2. 2
   Autrethe filtrate evaporated
3. 3
   Autrethe residue obtained
4. 4
   Autrechromatographed on silica gel (dichloromethanemethanol, 95:5 as eluant)

Mode opératoire

To a solution of diethyl (S)-[2-benzyloxy-1-(t-butyldiphenylsilyloxymethyl)ethoxy]methylphosphonate (1.90 g, 3.3 mmol) in ethanol (20 ml) containing a trace of methanol/HCl (10 drops), was added 10%Pd-C (1.2 g). The mixture was shaken under an atmosphere of hydrogen at ambient temperature and atmospheric pressure until hydrogen uptake was complete and t.l.c. (SiO2, CH2Cl2 -MeOH, 95:5) indicated no starting material remained. The reaction mixture was filtered, the filtrate evaporated and the residue obtained chromatographed on silica gel (dichloromethanemethanol, 95:5 as eluant) to give the title compound as a colourless oil (1.35 g, 84%).

Source