反应详情

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.

1. customthe reaction mixture was carefully quenched with brine
2. extractionextracted 3 times with Et2O
3. dry with materialThe combined organic extracts were dried over MgSO4
4. customThe solvent was removed under reduced pressure
5. customthe residue purified by flash chromatography (gradient hexane to hexane-EtOAc 91:9)