Diethyl Ether → HCID 16081324, compound

Participants

Reaction Conditions

Reaction Steps

A solution of EtMgBr in Et2O (3 M, 15 mL, 45 mmol) was added to a stirred solution of ZnCl2-Et2O (45% in DCM, 15 mL, 42 mmol) in THF (100 mL) at 0° C. under N2 and the solution stirred at 0° C. for 10 min. Pd(PPh3)4 (578 mg, 0.5 mmol) and iodide 66 (3.15 g, 10.1 mmol) were added and the mixture stirred at 0° C. for 1 h. The mixture was poured into ice/water (200 mL) and extracted with EtOAc (3×100 mL). The combined organic fraction was dried and the solvent evaporated. The residue was purified by chromatography, eluting with 30% EtOAc, to give 1-oxide 67 (1.20 g, 56%) as a pale yellow solid: mp (MeOH) 80-81° C.; 1H NMR δ 8.26 (s, 1H, H-9), 7.26 (s, 1H, H-5), 3.11 (q, J=7.2 Hz, 4H, H-6, H-8), 3.02 (q, J=7.6 Hz, 2H, CH2), 2.21 (p, J=7.2 Hz, 2H, H-7), 1.43 (t, J=7.6 Hz, 3H, CH3); 13C NMR δ 167.0, 154.6, 148.7, 147.6, 132.3, 122.7, 114.3, 33.2, 32.8, 30.6, 25.8, 12.4. Anal. calcd for C12H13N3O.¼CH3OH: C, 65.9; H, 6.3; N, 18.8. Found: C, 66.0; H, 6.1; N, 18.5%.

Provenance & Evidence