Allyltributylstannane → HCID 57786562, compound

Participants

Reaction Steps

Pd(PPh3)4 (0.89 g, 0.77 mmol) was added to a stirred, degassed solution of iodide 66 (4.80 g, 15.3 mmol) and allyltributyltin (5.2 mL, 16.9 mmol) in DME (100 mL), and the mixture stirred at reflux temperature for 8 h. The solvent was evaporated and the residue purified by chromatography, eluting with 10% EtOAc/pet. ether, to give 1-oxide 69 (2.96 g, 85%) as white solid: mp (EtOAc/pet. ether) 60-61° C.; 1H NMR δ 8.26 (s, 1H, H-9), 7.77 (s, 1H, H-5), 6.12-6.23 (m, 1H, H-2′), 5.29 (dd, J=17.1, 1.5 Hz, 1H, H-3′), 5.22 (dd, J=10.1, 1.3 Hz, 1H, H-3′), 3.77 (br d, J=6.9 Hz, 2H, H-1′), 3.08-3.14 (m, 4H, H-6, H-8), 2.21 (p, J=7.5 Hz, 2H, H-7); 13C NMR δ 164.1, 154.8, 149.0, 147.5, 133.0, 132.3, 122.7, 118.2, 114.3, 41.6, 33.2, 32.8, 25.7. Anal. calcd for C13H13N3O: C, 68.7; H, 5.8; N, 18.5. Found: C, 68.7; H, 5.9; N, 18.7%.

Provenance & Evidence