Sodium borohydride → (4-Iodo-2-methoxy-pyridin-3-yl)methanol

Participants

Reaction Steps

Following the procedure in Example 1, the reaction was carried out with 1b (1.88 g, 7.1 mmol) and NaBH4 (0.135 g, 3.56 mmol) in EtOH (40 mL) to afford 2b as a pale yellow oil (1.83 g, 97%). The crude product was sufficiently pure for the subsequent reaction. IR (CH2Cl2, NaCl,cm−1) 3391, 2946, 1561, 1459, 1380, 1019, 805; 1H NMR (300 MHz, CDCl3) δ2.43 (t, J=7 Hz,1H), 3.99 (s, 3H), 4.82 (d, J=7 Hz, 2H), 7.35 (d, J=5.4 Hz, 1H), 7.7 (d, J=5.4 Hz, 1H); 13C NMR (75 MHz, CDCl3) δ54.29, 64.90, 112.12, 126.50, 128.15, 146.59, 161.71; HRMS (EI) m/z calcd for C7H8NO2I (M+) 264.9600, found 264.9598; LRMS (EI) m/z 265 (M+, 53), 250(84), 138(30), 84(100), 78(30).

Provenance & Evidence