Toluene → t-Butyl {2-[4-(3-oxo-propenyl)-benzoylamino]-phenyl}-carbamate

Participants

Reaction Conditions

Reaction Steps

A stirred suspension of compound XI (4.00 g, 11.75 mmol), (triphenylphosphoranylidene)-acetaldehyde (3.60 g, 11.83 mmol) in anhydrous toluene (100 ml) was heated at 80° C. under nitrogen. After 2 days, the reaction mixture was concentrated and directly purified by flash chromatography on silica gel (AcOEt/hexane:30/70) to afford the title compound XVI (3.70 g, 10.10 mmol, 86% yield) as a yellow sticky solid (slightly contaminated with the diene). 1H NMR (300 MHz, CDCl3) δ(ppm): 9.75 (d, J=7.8 Hz, 1H), 9.49 (bs, 1H), AB system (δA=8.03, δB=7.65, J=8.4 Hz, 4H), 7.85–7.72 (m, 1H), 7.52 (d, J=15.6 Hz, 1H), 7.33–7.05 (m, 3H), 7.05–6.90 (m, 1H), 6.78 (dd, J=15.6, 7.8 Hz, 1H), 1.53 (s, 9H).

Provenance & Evidence