Sodium borohydride → HCID 137329845, compound

Participants

Reaction Steps

To a solution of 5-allyldimethylsilyl-2-pyridinecarboxaldehyde (8 Scheme 27, 3.1 g, 15 mmol) in EtOH (80 mL) was added sodium borohydride (1.1 g, 30 mmol) portion-wise for 10 min at room temperature. After further stirring for 30 min, excess sodium borohydride was quenched by slow addition of acetone (5 mL) to the reaction mixture. The solvent was evaporated and the residue was extracted with ethyl acetate/brine. The organic layer was dried (Na2SO4) and concentrated to afford an oil (2.7 g, 87%); 1H NMR (300 MHz, CDCl3) δ 0.27 (s, 6 H), 1.72 (dt, J=6.75, 1.05 Hz, 2 H), 4.74 (s, 2 H), 4.80 (dd, J=3.00, 1.20 Hz, 1 H), 4.48 (d, J=1.20 Hz, 1 H), 5.36 (bs, OH, 1 H), 5.69 (ddt, J=14.70, 9.30, 7.80 Hz, 1 H), 7.33 (d, J=7.80 Hz, 1 H), 7.76 (d, J=7.80 Hz, 1 H), 8.54 (s, 1 H), 13C NMR (75 MHz, CDCl3) −3.4 (2C), 23.5, 64.6 114.3, 120.6, 131.9, 133.9, 142.6, 153.0, 160.8. HRMS (EI) calcd for C11H17NOSi 207.1079, found 206.0999.

Provenance & Evidence