Triethyl phosphonoacetate → 3-{4-[Dimethylamino-(3-fluorophenyl)-methyl]-cyclohexyl}-acrylic acid ethyl ester

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Reaction Steps

Potassium tert-butylate (12.34 g, 0.11 mol) was added, under argon, to a solution of phosphonoacetic acid triethyl ester (24.66 g, 0.11 mol) in abs. DMF (200 ml), and the mixture was stirred for 10 minutes. The aldehyde 34 (19.3 g, 0.073 mol) dissolved in DMF (200 ml) was then added dropwise. The mixture was stirred for 3 h at RT and then poured onto ice. The reaction mixture was extracted with diethyl ether (3×200 ml) and the organic phase was washed with water and saturated NaCl solution, dried and concentrated in vacuo. The crude product was purified by flash chromatography with ethyl acetate/cyclohexane (1:2).

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