Triphenylphosphine → Ethyl acetate hexane

Participants

Reaction Steps

(5-Bromonaphthalen-1-yl)methanol (275 mg), PPh3 (456 mg, 1.5 eq.), and 1,3-bis(t-butoxycarbonyl)guanidine (601 mg, 2 eq.) in 5 mL toluene at 0° C. was added diisopropylazodicarboxylate (0.34 mL, 1.5 eq.) drop wise over 15 minutes. Reaction was stirred for 3 hours at room temperature then 2 drops H2O were added, and the solution was concentrated. Chromatography achieved using ISCO max gradient 20% EtOAc/hexane yielding product as a white solid (493 mg, 90% yield). 1H NMR (400 MHz) (CDCl3) δ 9.47 (bs, 2H), 8.11 (d, J=8 Hz, 1H), 7.91 (d, J=8 Hz, 1H), 7.73 (d, J=8 Hz, 1H), 7.46 (t, J=16 Hz, 1H), 7.28 (t, J=16 Hz, 1H), 7.16 (d, J=8 Hz, 1H), 5.62 (s, 2H), 1.36 (s, 9H), 1.07 (s, 9H). 13C NMR (100 MHz) (CDCl3) δ160.83, 154.95, 135.04, 131.95, 129.89, 126.71, 126.26, 126.16, 123.71, 122.87, 122.73, 84.19, 79.03, 45.10, 28.23, 27.61.

Provenance & Evidence