Tetrahydrofuran → HCID 69416089, compound

Participants

Reaction Steps

Methyl (triphenylphosphoranylidene)acetate (1.16 g, 3.465 mmol) and {1-formyl-2-[1-(3-phenyl-allyl)-1H-indol-3-yl]-ethyl}-carbamic acid tert-butyl ester (1.4 g, 3.465 mmol) in THF (19 mL) were stirred overnight under argon. The solvent was removed, Et2O added and the solution filtered. The filtrate was concentrated and the residue subject to column chromatography (silica gel, 25% EtOAc/petroleum ether) to afford the title compound (1.238 g, 78%), mp 119.3-120.6° C. 1H NMR (CDCl3) δ 7.59 (1H, d, J=7.71 Hz), 7.36-7.01 (9H, m), 6.97 (1H, s), 6.45 (1H, d, J=6.45 Hz), 6.29 (1H, dt, J=5.58 15.93 Hz), 5.88 (1H, d, J=15.93 Hz), 4.82 (2H, d, J=5.4 Hz), 4.69 (1H, br s), 3.65 (3H, s), 3.04 (2H, br s), 1.38 (9H, s), 13C NMR (CDCl3) δ 166.6, 155.1, 148.7, 136.4, 136.1, 132.3, 128.5, 128.2, 127.8, 126.4, 124.7, 121.8, 120.4, 119.3, 119.0, 109.6, 109.5, 79.7, 51.7, 51.5, 48.2, 30.4, 28.2. ISMS: 461 (M+H).

Provenance & Evidence