Coumarin 343 → Coumarin propyl azide

Participants

Reaction Conditions

Reaction Steps

A solution of Coumarin 343 (0.285 g, 1.00 mmol) and 3-azido-1-propanol (0.505 g, 5.00 mmol) in CH2Cl2 (20 mL) was cooled to 0° C. and EDC.HCl (0.575 g, 3.00 mmol) and DMAP (0.006 g, 0.05 mmol) were sequentially added. The orange solution was stirred at 0° C. for 2 h, then at ambient temperature overnight. The reaction mixture was washed with water (2×50 mL) and dried over MgSO4. The volatiles were removed under reduced pressure and the crude product purified by flash chromatography (CC, SiO2, 1) 100% CH2Cl2; 2) CH2Cl2/Et2O 10:1). The isolated product still contained some 3-azido-1-propanol starting material, which was then removed by coevaporation with toluene under reduced pressure. Obtained 0.110 g (0.299 mmol, 30%) of (28) as an orange oil that partially solidified by standing at ambient temperature over several days.

Provenance & Evidence