Benzaldehyde → Dibenzyl P-[alpha-(N-Benzyl-N-hydroxyamino)benzyl]phosphonate

Participants

Reaction Conditions

Reaction Steps

Using the procedure of Example 1, the title compound is prepared from 15.0 g (94 mmol) of N-benzylhydroxylamine hydrochloride, 10.6 g (100 mmol) of benzaldehyde, 26.7 g (100 mmol) of dibenzyl phosphite, 3.78 g (45 mmol) of sodium bicarbonate and 300 ml of THF by heating at 60° C. for four hours. The residue is purified by column chromatography (silica gel, 2.5:1 hexane:ethyl acetate eluent) followed by recrystallization from a mixture of methylene chloride and hexane to give 5.6 g (13% yield) of a white solid melting at 116°-118° C.

Provenance & Evidence