Sodium borohydride → HCID 117992744, compound

Participants

Reaction Steps

To a solution of crude ethyl 2-(6-chloro-2-methoxypyridin-3-yl)acrylate (203 g, 0.84 mol) in MeOH (2 L) was added NaBH4 (63.8 g, 1.68 mol) in portions at 0° C. After addition, the reaction mixture was allowed to warm to r.t. over 2 h. The reaction solvent was removed under reduced pressure. The residue was treated with water and extracted with EtOAc twice. The combined organic extracts were washed with brine, dried over Na2SO4 and concentrated. The crude product was purified by silica gel column chromatography (Petroleum ether→Petroleum ether:EtOAc=10:1) to afford ethyl 2-(6-chloro-2-methoxypyridin-3-yl)propanoate (126.5 g 62%) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 1.21 (t, 3H), 1.44 (d, 3H), 3.88 (q, 1H), 3.95 (s, 3H), 4.13 (q, 2H), 6.89 (d, 1H), 7.46 (d, 1H).

Provenance & Evidence