3-Benzyloxy-2-methyl-1-(2-pivaloyloxyethyl)pyridin-4-one → 3-Hydroxy-2-methyl-1-(2-pivaloyloxyethyl)pyridin-4-one

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Reaction Steps

3-Benzyloxy-2-methyl-1-(2-pivaloyloxyethyl)pyridin-4-one (1.08 g, 0.003 mol) was hydrogenated over Pd/C catalyst in dimethylformamide (30 ml) with stirring for 24 hours. The solution was filtered and rotary evaporated to dryness to provide a crude product (1.08 g) which was flash chromatographed (silica gel, Kieselgel 60,7734, 20 mm×300 mm column, eluting with ethyl acetate:ethanol, 1:1 v/v). Rotary evaporation in vacuo at 60° C. provided the title compound in 77.46% yield as orange crystals, m.p. 147°-149° C.; νmax 1580, 1625, 1725, 2850 cm-1 ; δ(d6 dimethylsulphoxide) 1.1 (9H,s), 2.35 (3H,s), 4.30 (4H,s), 4.4 (1H,s), 6.15 (1H,d), 7.55 (1H,d).

Provenance & Evidence