Ethyl Acetate → 1-(2,2-Dimethoxyethoxy)-4-fluoro-3-methylbenzene

Participants

Reaction Steps

A solution of diethyl cyanophosphonate (2.79 g) in dry tetrahydrofuran (10 ml) was added to a suspension of sodium hydride (60% oil dispersion; 0.63 g) in THF (16 ml) over 5 mins with ice cooling. After 15 min, a solution of 5-fluorobenzofuran-4-carbaldehyde (2.15 g) in THF (10 ml) was added and after 5 mins the solution was warmed up and stirred at room temperature for 3 h. Brine (20 ml) and ethyl acetate (20 ml) were added, the phases separated and the aqueous extracted with ethyl acetate (2×25 ml). The extracts were dried and evaporated and the residue purified by chromatography (Biotage Flash 40; 90 g; ethyl acetate:hexane 1:9) to give the title compound as a cream solid (1.97 g)

Provenance & Evidence