Triphenylphosphine → Ethyl acetate hexane

Participants

Reaction Steps

(5-(2-Methyl-4-(trifluoromethyl)phenyl)naphthalen-1-yl)methanol (67 mg), PPh3 (83 mg, 1.5 eq.), and 1,3-bis(t-butoxycarbonyl)guanidine (110 mg, 2 eq.) in 3 mL toluene at 0° C. was added diisopropylazodicarboxylate (0.06 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 30% EtOAc/hexane yielding product as a clear oil (93 mg, 79% yield). 1H NMR (400 MHz) (CDCl3) δ 9.55 (bs, 2H), 8.10 (d, J=8 Hz, 1H), 7.62-7.57 (m, 3H), 7.41-7.22 (m, 5H), 5.84-5.74 (m, 2H), 2.06 (s, 3H), 1.48 (s, 9H), 1.17 (s, 9H). 13C NMR (100 MHz) (CDCl3) δ163.80, 160.97, 155.04, 138.98, 137.77, 135.08, 131.60, 130.85, 130.69, 126.61, 126.20, 125.71, 125.37, 124.60, 122.88, 122.45, 122.23, 84.03, 78.99, 45.23, 28.26, 27.57, 19.93.

Provenance & Evidence