Methyl iodide → HCID 90064484, compound

Participants

Reaction Conditions

Reaction Steps

To a reaction vessel, 30 g (0.077 mol) compound XII and 300 ml tetrahydrofuran were added under nitrogen, the mixture was cooled to −10-−15° C., 78 ml (0.16 mol, 2 mol/L) solution of lithium diisopropylamide in n-heptane was added dropwise for about 30 min, after the addition was complete, the reaction was kept at this temperature for 30 min, 4.8 ml (0.077 mol) iodomethane was added dropwise, after the addition was complete, the mixture was warmed to room temperature and stirred for 2 h, 600 ml ethyl acetate and 300 ml water were added, extracted, the organic layer was collected, dried over sodium sulfate, filtered, the filtrate was concentrated to dry under reduced pressure, separated by column chromatography, and 14.5 g compound XIII was obtained, with yield of 46.7%. 1H NMR (CDCl3): δ 1.07-1.21 (m, 2H), 1.41 (d, 3H, J=6.7 Hz), 1.45 (s, 10H), 1.55 (q, 2H, J=7.4 Hz), 1.66-1.69 (m, 1H), 1.80-1.83 (m, 1H), 2.64-2.71 (m, 2H), 3.17-3.24 (m, 1H), 3.92-4.00 (m, 1H), 4.06-4.09 (m, 2H), 4.41 (q, 1H, J=6.7 Hz), 6.05 (s, 2H), 6.82 (s, 1H), 7.20 (s, 1H); MS (ESI): m/z 403 [M+H]+.

Provenance & Evidence