Chloromethyl Methyl Ether → 4-Iodo-2-methoxy-3-methoxymethoxymethylpyridine

Participants

Reaction Steps

Following the procedure in Example 2, the reaction was carried out with 2b (1.77 g, 6.68 mmol), MOMCl (1.52 mL, 20 mmol) and iPr2EtN (3.49 mL, 20 mmol) in dry CH2Cl2 (40 mL) to afford 3b as an orange-yellow oil (2.06 g, 100%). The crude product was sufficiently pure for the subsequent reaction. IR (CH2Cl2, NaCl, cm−1) 2949, 1561, 1459, 1380, 1265, 1039, 741; 1H NMR (300 MHz, CDCl3) δ3.45 (s, 3H), 3.96 (s, 3H), 4.72 (s, 2H), 4.75 (s, 2H), 7.35 (d,J=5.4 Hz, 1H), 7.71 (d,J=5.4 Hz, 1H); 13C NMR (75 MHz, CDCl3) δ54.35, 55.80, 67.89, 96.70, 114.20, 123.97, 128.10, 147.11, 162.39; HRMS (EI) m/z calcd for C9H12NO3I (M+) 308.9862, found 308.9860; LRMS (EI) m/z 309(M+, 19), 277(20), 264(45), 248(100), 218(68), 152(39), 92(50), 79(35).

Provenance & Evidence