2-Naphthalenecarboxaldehyde → HCID 67393249, compound

Participants

Reaction Steps

To a solution of methyl 4-[(diethoxyphosphoryl)methyl]benzoate (916 mg, 3.20 mmol; see Preparation 4(i) above) in THF (20 mL, dry) under nitrogen atmosphere was added a sodium hydride (520 mg, 60% dispersion in oil, 13.00 mmol) at 0° C. 2-Naphthaldehyde (500 mg, 3.20 mmol) was dissolved in THF (10 mL, dry) then added dropwise to the reaction mixture at 0° C. under N2 and the reaction mixture stirred at room temperature for 1 h followed by quenching with water. The pH level of the mixture was adjusted to pH 4 by the dropwise addition of HCl(conc.) with stirring at 0° C. TLC analysis showed that it was the required product (282 mg). Extraction of the water layer with ethyl acetate followed by drying (MgSO4) gave the sub-title compound (total amount 846 mg, 92%), m.p.=195-198° C.

Provenance & Evidence