Triphenylphosphine (59.7 g, 227.7 mmol) was slowly added to a stirred solution of azide 23 (55.2 g, 178.4 mmol) in anhydrous tetrahydrofuran (700 mL) at 0 °C. The reaction mixture was stirred continuously for 10 hours at room temperature. Subsequently, water (5.8 mL, 323.4 mmol) was added to hydrolyze the intermediate phosphorus adduct. After continued stirring for 10 hours, the reaction mixture was diluted with water (1000 mL) and washed with toluene (200 mL, twice). The aqueous phase was concentrated by evaporation to afford the target product 1-phenyl-2,5,8,11-tetraoxatridecan-13-amine (50.6 g, 91% yield). The product was characterized by 1HNMR (400 MHz, CD3OD): δ 7.11-7.29 (m, 5H), 4.51 (s, 2H), 3.55-3.64 (m, 12H), 3.43 (t, J=5.2Hz, 2H), 2.78 (t, J=5.2Hz, 2H).
