Methyl iodide → HCID 12994066, compound

Participants

Reaction Steps

Through use of General Procedure II, NaH (0.110 g 4.6 mmol), methyl iodide (0.65 mL, 4.6 mmol), and 2-[(1-hydroxycyclohexyl)]-1,10-phenanthroline (0.320 g, 1.15 mmol), prepared as described by Example 1, were reacted to provide 0.301 g (90% yield) of the title methyl ether as a colorless oil: 1H NMR (300 MHz, CDCl3) δ9.24 (dd, J=4.50, 1.80 Hz, Hp9), 8.25 (d, J=8.40 Hz, Hp4, dd, J=8.10, 2.40 Hz, Hp7), 7.96 (d, J=8.40 Hz, Hp3), 7.82 and 7.75 (two d, J=8.80 Hz, Hp5 and Hp6), 7.61 (dd, J=8.10, 4.50 Hz, Hp8), 3.11 (s, 3H, OCH3), 2.23 (m, 4H, cyclohexyl H), 1.74 (m, 6H, cyclohexyl H); 13C NMR (75 MHz) δ166.33, 150.49, 146.33, 145.11, 136.40, 136.04, 128.77, 127.41, 126.38, 126.03, 122.40, 120.45, 80.46, 50.45, 33.83, 25.08, 21.69; IR (CHCl3) 3048 (C—H Ar), 2933 ((CH), 908 (C—H Ar), cm−1; HRMS m/e Calcd for C19H21N2O (MH+): 293.1654, found: 293.1665.

Provenance & Evidence