N-(6-formylpyridin-2-yl)-2,2-dimethylpropanamide → N-[6-(1-Hydroxyethyl)pyridin-2-yl]-2,2-dimethylpropanamide

Participants

Reaction Steps

To an ice-cooled solution of N-(6-formylpyridin-2-yl)-2,2-dimethylpropanamide (4.0 g, 19.4 mmol) in tetrahydrofuran (30 mL) was added methylmagnesium chloride (13.6 mL, 40.7 mmol, 3 M in THF) dropwise. After 2 h the reaction was quenched with saturated aqueous NH4Cl solution (10 mL) and diluted with ethyl acetate (50 mL). The mixture was washed with saturated aqueous NaHCO3 solution (2×50 mL). The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated. The resulting residue was purified by flash column chromatography (2:1 hexanes/EtOAc) to afford the intermediate as a clear oil (0.56 g, 49%). 1H NMR (400 MHz, CDCl3), δ: 8.14 (d, J=8.1 Hz, 1H), 8.00 (br s, 1H), 7.70 (t, J=7.8 Hz, 1H), 7.00 (d, J=7.5 Hz, 1H), 4.82 (m, 1H), 3.81 (d, J=5.0 Hz, 1H), 1.49 (d, J=6.5 Hz, 3H), 1.35 (s, 9H); LRMS (ESI): m/z: 223.2.

Provenance & Evidence