Methane → 3-Benzyloxy-2-ethyl-1-[2-(alpha-methylpropionyloxy)ethyl]pyridin-4-one

Participants

Reaction Steps

3-Benzyloxy-2-ethyl-1-(2-hydroxyethyl)pyridin-4-one (0.92 g, 0.003 mole, prepared as described in Example 2), was dissolved in a mixture of 30 ml dimethylformamide and 20 ml of pyridine at room temperature whilst stirring under N2. The solution was added dropwise to a mixture of isobutyryl chloride (1.3 ml, 0.012 mole) in 10 ml of pyridine at 0° C. and the resulting solution was then stirred at room temperature overnight under N2. The reaction was monitored by tlc (silica; 50% EtOH:50% EtOAc). The solution was filtered, the dimethylformamide was removed under high vacuum by rotary evaporation and the oily residue was dissolved in 100 ml of dichloromethane. The solution was washed with 5% w/v aqueous NaHCO3 (3×100 ml) and water (2×100 ml). The organic layer was dried over Na2SO4, filtered and rotary evaporated to give a crude oil. This was treated with activated charcoal in ethyl acetate, filtered and rotary evaporated. The oil produced was purified by means of column chromatography (silica; 50% EtOH:50% EtOAc). Rotary evaporation of the selected samples gave the title compound as an oil in 66% yield, δ(CDCl3), 0.9-1.3 (9H, m), 2.3-2.7 (3H, m), 3.5-4.3 (4H, m), 5.2 (2H, s), 6.2-6.4 (1H, d, 7 Hz), 7.1-7.5 (6H, m).

Provenance & Evidence