反应详情

To a suspension of 10.7 g (0.02 mol) 3-(octadecyloxy)-5-(3-phenoxypropoxy)benzoic acid in 250 ml of anhydrous toluene cooled in an ice bath was added 5.1 ml (0.024 mol) of diphenylphosphoryl azide followed by 3.8 ml (0.028 mol) of triethylamine. The reaction mixture was stirred in an ice bath for 1 hour and then heated at 90° for 2 hours. After cooling to room temperature, 70 ml of benzyl alcohol was added. The reaction mixture was then stirred and heated at 90° for 18 hours. The solvent was removed at reduced pressure and the residue was dissolved in ethyl acetate. The extract was washed with saturated NaHCO3 solution, dried and concentrated to an oil which was purified by HPLC using 10% ethyl acetate-hexane to give 10.9 g (85% yield, mp 68°-69°) of 3-(octadecyloxy)-5-(3-phenoxypropoxy)phenylcarbamic acid phenylmethyl ester. The structure was confirmed by nmr and mass spectra.

1. temperaturecooled in an ice bath
2. temperatureheated at 90° for 2 hours
3. stirringThe reaction mixture was then stirred
4. temperatureheated at 90° for 18 hours
5. customThe solvent was removed at reduced pressure
6. dissolutionthe residue was dissolved in ethyl acetate
7. washThe extract was washed with saturated NaHCO3 solution
8. customdried
9. concentrationconcentrated to an oil which
10. customwas purified by HPLC