Sodium hydride → 4-Benzyl-2-{4-[2-(2,6-dichloro-phenyl)-vinyl]-phenyl}-morpholine

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Reaction Steps

To a suspension of (2,6-dichloro-benzyl)-triphenyl-phosphonium bromide (2.06 g; 4.1 mmol) (See: A. Schmidpeter, H. Noeth, G. Jochem, H.-P. Schroedel, K. Karaghiosoff; Chem. Ber., 1995, 128, 379) in THF (25 mL) was added sodium hydride (60% dispersion in mineral oil) (215 mg; 4.5 mmol), at 0° C. After stirring for 1 hour, 4-(4-benzyl-morpholin-2-yl)-benzaldehyde (1.05 g; 3.7 mmol) was added, at 0° C. Subsequently, the resulting mixture was heated under reflux for 1 hour. After cooling to RT, 5% aqueous NaHCO3 was added and the mixture extracted with Et2O. The organic layer was dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by column chromatography (SiO2, Et2O:hexanes 1:1) to afford 4-benzyl-2-{4-[2-(2,6-dichloro-phenyl)-vinyl]-phenyl}-morpholine (1.15 g).

Provenance & Evidence