Iodoethane → HCID 178477467, compound

Participants

Reaction Steps

A solution of compound 65 (0.2 g, 0.698 mmol) in acetone (10 mL) was treated with iodoethane (0.33 mL, 4.189 mmol) at room temperature and the resulting solution was refluxed for 4 h. The reaction was brought to room temperature, and solvent was evaporated. The crude was diluted with sat. NaHCO3 solution (20 mL) and compound was extracted into CH2Cl2 (3×20 mL). The combined CH2Cl2 layer was washed with brine (15 mL) and dried (Na2SO4). Evaporation of solvent and purification of crude by column chromatography (2 M NH3 in methanol: CH2Cl2, 5:95) to obtain compound 66 (0.055 g, 25%) as a solid. mp 77-79° C.; 1H NMR (DMSO-d6) δ 1.20-1.30 (m, 3H), 2.28 (s, 3H), 2.50-2.57 (m, 4H), 2.90-2.96 (m, 2H), 3.02-3.06 (m, 2H), 5.98-6.04 (m, 2H), 6.60-6.63 (m, 1H), 7.17-7.35 (m, 4H), 10.90 (s, 1H); ESI-MS m/z (%):: 315 (M+, 66), 311 (78), 249 (100).

Provenance & Evidence