Sodium hydride → HCID 86757409, compound

Participants

Reaction Steps

To a solution of washed NaH (0.74 g, 30.94 mmol)) in THF (30 mL) is added a solution of diethyl [2-(diethylamino)-2-oxoethyl]-phosphonate (7.77 g, 30.94 mmol) in THF (30 mol), dropwise, and the solution is stirred at room temperature for 5 minutes until gas evolution ceases. A solution of 4′-(2,6-difluorobenzyloxy)-3′-[3-(tetrahydropyran-2-yloxy)-propoxy]-acetophenone (6.50 g, 15.47 mmol) in THF (30 mL) is then added over 5 minutes and the resulting mixture is refluxed for 18 hours. After cooling, the mixture is quenched with 30 mL saturated aqueous NH4Cl, and is concentrated to 30 mL in vacuo. The residue is dissolved in EtOAc (50 mL), washed with H2O (1×50 mL) and brine (1×50 ml), dried over MgSO4, and concentrated in vacuo. Chromatography (silica, 3:1 hexane/EtOAc) provides N,N-diethyl (E)-3-{4-(2,6-difluorobenzyloxy)-3-[3-(tetrahydropyran-2-yloxy)-propoxy]-phenyl}-2-butenamide.

Provenance & Evidence