Benzyl Alcohol → HCID 53760467, compound

Participants

Reaction Steps

To 2.55 g (4.36 mmol) of 3-[3-carboxy-5-(octadecyloxy)phenoxy]propylphosphonic acid diethyl ester in 75 ml of toluene stirred and cooled in an ice bath was added 1.12 ml (5.23 mmol) of diphenylphosphoryl azide followed by 0.73 ml (5.23 mmol) of triethylamine added dropwise. After stirring in the ice bath for 2 hours, the reaction mixture was stirred and heated at 90° for 2 hours. Benzyl alcohol (16 ml) was added and heating at 90° was continued for 4 hours. The solvent and the excess benzyl alcohol were removed at reduced pressure and the residue was dissolved in ethyl acetate. The extract was washed with NaHCO3 solution, dried and concentrated at reduced pressure to an oil which was purified by HPLC using 50% ethyl acetate-hexane to give 2.47 g (82% yield) of [3-[3-(diethoxyphosphinyl)propoxy]-5-(octadecyloxy)-phenyl]carbamic acid phenylmethyl ester as an oil. The structure was confirmed by nmr and mass spectra.

Provenance & Evidence