Allyl Alcohol → N-(6-nitro-2,3-dihydro-1H-inden-5-yl)acetamide

Participants

Reaction Conditions

Reaction Steps

Iodide 100 (1.53 g, 4.7 mmol) was added to a degassed solution of allyl alcohol (0.89 mL, 13.1 mmol), Pd(OAc)2 (52 mg, 0.23 mmol), nBu4NBr (1.35 g, 4.2 mmol) and NaHCO3 (0.86 g, 10.3 mmol) in DMF (40 mL) and the solution was stirred at 50° C. for 24 h under N2. The mixture was quenched with saturated aqueous NH4Cl solution (50 mL) and filtered. The filtrate was extracted with EtOAc (5×50 mL), dried and the solvent evaporated. The residue was purified by chromatography, eluting with a gradient (20-50%) of EtOAc/pet. ether, to give (i) starting material 100 (0.86 g, 56%) and (ii) aldehyde 101 as an orange gum: 1H NMR δ 9.93 (s, 1H, CHO), 8.21 (s, 1H, H-9), 7.69 (s, 1H, H-5), 3.35 (t, J=7.0 Hz, 2H, CH2), 3.20-3.27 (m, 2H, CH2), 3.19 (br dd, J=7.2, 6.7 Hz, 2H, CH2), 2.64-2.76 (m, 3H, H-7, CH2), 1.19 (d, J=6.4 Hz, 3H, CH3); 13C NMR δ 200.5, 163.9, 154.5, 148.7, 147.3, 132.4, 122.8, 114.4, 41.2, 40.9, 40.5, 35.0, 29.4, 20.2; MS (FAB+) m/z 258 (MH+, 60%), 242 (10); HRMS (FAB+) calcd for C14H16N3O2 (MH+) m/z 258.1243, found 258.1242.

Provenance & Evidence