تفاعل #6353

معادلة التفاعل

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

hydrogen

CH2Cl2 MeOH

→

title compound

المردود 85.1%

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

المردود 85.1%

المذيبات

ethanol

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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%).

المصدر