Sodium borohydride → 3-Pyridinemethanol, 4-iodo-2-methoxy-6-(trimethylsilyl)-

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Reaction Steps

To a solution of NaBH4 (1.1 g, 26.4 mmol) in EtOH (100 mL) at −40° C. was slowly added a solution of 4-iodo-2-methoxy-6-trimethylsilanyl-3-pyridinecarboxaldehyde 1 (31.8 g, 94.9 mmol) in EtOH (50 mL). See Josien, H.; Ko, S.-B.; Bom, D.; Curran, D. P. Chem. Eur. J., 67 (1998). After stirring for 1 h, the reaction mixture was carefully quenched with brine and then extracted 3 times with Et2O. The combined organic extracts were dried over MgSO4. The solvent was removed under reduced pressure and the residue purified by flash chromatography (gradient hexane to hexane-EtOAc 91:9) to afford 2a (25.1 g, 78% yield) as a clear oil. 1H NMR (300 MHz, CDCl3) δ0.28 (s, 9H), 2.5 (bs, 1H), 4.01 (s, 3H), 4.8 (s, 2H), 7.5 (s, 1H); 13C NMR (75 MHz, CDCl3) δ−1.99, 53.78, 65.32, 11.65, 125.34, 133.19, 160.9, 165.81; IR (film, NaCl, cm−1) 3485, 2960, 1580, 1450, 1039, 839; LRMS (70 eV, EI) m/z (rel int %) 337 (M+), 322 (100), 306, 194, 180, 73. HRMS m/z calcd for C10H16NO2SiI (M+) 336.9996, found 337.000.

Provenance & Evidence