Allyl bromide → tert-butyl 3-(3-(2-allyl-2H-tetrazol-5-yl)phenethoxy)propanoate

Participants

Reaction Conditions

Reaction Steps

Allyl bromide (0.4 mL) was added in one portion to tert-butyl 3-(3-(2H-tetrazol-5-yl)phenethoxy)propanoate [Example 7, Step ii)] (1.05 g) and potassium carbonate (905 mg) in acetonitrile (10 mL). The resulting mixture was stirred at 65° C. for 1 h. After cooling to rt, the reaction mixture was diluted with ethyl acetate (50 mL) and washed with water (1×20 mL). The organic was dried over magnesium sulfate, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 80% ethyl acetate in isohexane to afford the subtitled compounds tert-butyl 3-(3-(2-allyl-2H-tetrazol-5-yl)phenethoxy)propanoate (427 mg) and tert-butyl 3-(3-(1-allyl-1H-tetrazol-5-yl)phenethoxy)propanoate (136 mg). Tert-butyl 3-(3-(2-allyl-2H-tetrazol-5-yl)phenethoxy)propanoate: 1H NMR (300 MHz, CDCl3) δ 8.02-7.96 (m, 2H), 7.44-7.30 (m, 2H), 6.12 (m, 1H), 5.45-5.37 (m, 2H), 5.26 (dt, J=6.2, 1.4 Hz, 2H), 3.70 (t, J=7.1 Hz, 2H), 3.70 (t, J=6.5 Hz, 2H), 2.95 (t, J=7.1 Hz, 2H), 2.49 (t, J=6.5 Hz, 2H), 1.43 (s, 9H). Tert-butyl 3-(3-(1-allyl-1H-tetrazol-5-yl)phenethoxy)propanoate: 1H NMR (300 MHz, CDCl3) δ 7.59 (s, 1H), 7.56-7.39 (m, 3H), 6.07 (ddt, J=5.5, 10.6 and 17.2 Hz, 1H), 5.39 (dt, J=1.5 and 10.4 Hz, 1H), 5.16 (dt, J=1.8 and 17.1 Hz, 1H), 5.06 (dt, J=1.6 and 5.5 Hz, 2H), 3.70 (t, J=6.7 Hz, 2H), 3.68 (t, J=6.4 Hz, 2H), 2.95 (t, J=6.8 Hz, 2H), 2.46 (t, J=6.4 Hz, 2H), 1.41 (s, 9H).

Provenance & Evidence