Chloromethyl Methyl Ether → HCID 25228375, compound

Participants

Reaction Steps

Referring to FIG. 20, under a nitrogen atmosphere, triethylamine (0.034 mL, 0.235 mmol) and chloromethyl methyl ether (0.018 mL, 0.235 mmol) were added to a solution of 5b (0.0200 g, 0.109 mmol) in acetone (8 mL). The reaction was stirred for 1 h. The solvent was evaporated and the remaining residue was dissolved in chloroform, which was washed with brine, dried over Na2SO4, and evaporated to afford 8b (0.0236 g, 0.106 mmol, 97%) as a white solid: 1H NMR (CDCl3) δ 8.02 (1H, d, J=8.0 Hz), 7.93 (1H, d, J=9.2 Hz), 7.48 (1H, d, J=9.2 Hz), 7.29 (1H, d, J=8.4 Hz), 5.43 (2H, s), 3.58 (3H, s), 2.79 (3H, s); 13C NMR (CDCl3) δ 162.4, 161.8, 148.7, 135.9, 133.4, 121.8, 121.7, 114.6, 114.9, 95.1, 56.9, 25.7; FTIR (neat) 2924, 2216, 1612, 1504, 1248, 1161, 1143, 1061, 984, 924, 839 cm−1; MS (ESI) m/z calculated for (C13H12N2O2+H)+ 229, found 229; HRMS (ESI) m/z calculated for (C13H12N2O2+H)+ 229.0978, found 229.0996.

Provenance & Evidence