3-Methoxybenzaldehyde → HCID 67392783, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3-[(diethoxyphosphoryl)methyl]benzoate (1.02 g, 3.56 mmol; see step (i) above) in THF (5 mL, dry) under a nitrogen atmosphere was added sodium hydride (0.212 g, 60%, 18.8 mmol). After cooling the reaction mixture to 0° C., m-anisaldehyde (0.485 g, 3.56 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 was extracted with ethyl acetate and the organic layers were combined, dried (MgSO4), filtered and the solvent removed under reduced pressure. The product was purified using silica gel column chromatography (RF=0.80 20% ethyl acetate/n-hexane) to give the sub-title compound as a white solid (0.747 g, 78%), m.p.=92-94° C.

Provenance & Evidence