Ethyl Acetate → (e)-3-(6-Methoxy-[1,5]naphthyridin-4-yl)-acrylic acid ethyl ester

Participants

Reaction Steps

Triethylphosphonoacetate (7.3 g, 32.6 mmol) was added to a suspension of a NaH dispersion (1.4 g, 32.5 mmol, 55% in paraffin) in THF (40 mL) at 0° C. The mixture was stirred at 0° C. for 20 min before the dropwise addition of 6-methoxy-[1,5]naphthyridine-4-carbaldehyde (4.0 g, 21.3 mmol; prepared as in WO 2006/032466) in THF. The mixture was stirred at rt for 5 h, diluted with water and EA. The phases were separated and the aq. phase extracted with EA (2 times 50 mL). The combined org. phases were washed with brine, dried over MgSO4 and concentrated. The residue was purified by chromatography on SiO2 (Hex/EA 1:1) to give the desired alkene as a colourless solid (3.0 g, 56% yield).

Provenance & Evidence