Isopropyl iodide → tert-Butyl 3-(3-(1-isopropyl-1H-1,2,3-triazol-4-yl)phenethoxy)propanoate

Participants

Reaction Conditions

Reaction Steps

2-Iodopropane (0.168 mL) was added in one portion to a mixture tert-butyl 3-(3-ethynylphenethoxy)propanoate [Example 4, Step ii)] (383 mg), sodium azide (109 mg), tert-butanol (0.75 mL), water (3 mL) and copper(I) iodide (26.6 mg) and sealed into a microwave tube. The reaction was heated to 80° C., over a period of 3 h in the microwave reactor. The reaction mixture was diluted with ethyl acetate and 35% ammonia (1 mL) and ethyl acetate (2 mL) were added. The mixture was stirred for 30 min. and extracted into ethyl acetate. The organic was evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 20 to 100% ethyl acetate in isohexane to afford the titled compound (291 mg) as an oil. 1H NMR (300 MHz, CDCl3) δ 7.79 (s, 1H), 7.72-7.64 (m, 2H), 7.33 (t, J=7.6 Hz, 1H), 7.18 (d, J=7.5 Hz, 1H), 4.89 (septet, J=6.6 Hz, 1H), 3.70 (t, J=6.4 Hz, 2H), 3.697 (t, J=7.3 Hz, 2H), 2.92 (t, J=7.1 Hz, 2H), 2.49 (t, J=6.4 Hz, 2H), 1.63 (d, J=6.7 Hz, 6H), 1.43 (s, 9H)

Provenance & Evidence