Sodium hydride → HCID 67392595, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 4-[(diethoxyphosphoryl)methyl]benzoate (0.911 g, 3.18 mmol; see Preparation 4(i) above) in THF (10 mL, dry) under a nitrogen atmosphere was added sodium hydride (0.678 g, 60%, 18.8 mmol). After cooling the reaction mixture to 0° C., quinoline-3-aldehyde (0.500 g, 3.18 mmol) in THF (10 mL, dry) was carefully added dropwise with stirring. The reaction mixture was stirred for 1 h at room temperature and then quenched with water. After neutralisation with dilute HCl, the two layers were separated, the water layer extracted with ethyl acetate and the organic layers were combined, dried (MgSO4), filtered and the solvent removed under reduced pressure to give a white solid. The product was purified by silica gel column chromatography using 25% ethyl acetate/n-hexane (RF=0.50) to give the sub-title compound (0.900 g, 98%), as a white solid, m.p.=92-94° C.

Provenance & Evidence