tert-Butyl (2E)-3-(5-benzyloxy-6-methylpyridin-2-yl)acrylate → tert-Butyl 3-(5-hydroxy-6-methylpyridin-2-yl)propanoate

Participants

Reaction Steps

A solution of 700 mg (2.15 mmol) of tert-butyl (2E)-3-(5-benzyloxy-6-methylpyridin-2-yl)acrylate (from Step C) and 100 mg of 20% palladium hydroxide on carbon in 20 mL of EtOH was stirred under 1 atm of H2 overnight. The catalyst was filtered off through a cake of Celite and washed extensively with EtOAc. The filtrate was concentrated. Chromatography on a Biotage 40M cartridge using 7:13 v/v EtOAc/hexanes as the eluant afforded 450 mg of the title compound: 1H NMR (500 MHz, CDCl3) δ 1.41 (s, 9H), 2.49 (s, 3H), 2.63 (d, J=7.4, 2H), 2.98 (d, J=7.4, 2H), 6.90 (d, J=8.3, 1H), 7.05 (d, J=8.3, 1H).

Provenance & Evidence