Hydrochloric Acid → HCID 18334147, compound

Participants

Reaction Steps

Triphenylphosphinie (20.5 g) was added in small portions to a solution of α-(4-methoxyphenyl)-3-nitrobenzyl azide (18.5 g) [prepared as described in step (a) above] in anhydrous tetrahydrofuran (100 ml). When the triphenylphosphine was dissolved and the evolution of nitrogen had ceased, water (20 ml) was added to the reaction mixture and this mixture was heated under reflux for 6 hours. At the end of this time, the tetrahydrofuran of the reaction mixture was removed by evaporation under reduced pressure. The residue was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated by evaporation under reduced pressure. The residue was purified by chromatography through a silica gel column using a 2:1 by volume mixture of hexane and ethyl acetate as the eluant, to afford a colorless oil. This oil was dissolved in a solution of hydrogen chloride in ethyl acetate (4N). The ethyl acetate was evaporated to dryness. The residue was suspended in diisopropyl ether and filtered to afford the title compound (13.8 g) as a white solid.

Provenance & Evidence