2-Naphthalenecarboxaldehyde → HCID 13900156, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of acetonitrile (2.46 g, 60 mmol, 3.13 mL) in THF (300 mL) at -78° C. was added N-BuLi (37.5 mL, 60 mmol, 1.6M) dropwise over 30 minutes. The resulting solution was stirred at -78° C. for 15 minutes and then 2-naphthaldehyde (6.24 g, 40 mmol) in THF (50 mL) was added dropwise over 45 minutes. The resulting mixture was stirred for an additional 20 minutes at -78° C. and quenched at -78° C. by the addition of saturated NH4Cl (60 mL). The mixture was warmed to room temperature and the THF removed in vacuo to give a white solid. The residue was partitioned between CH2Cl2 (250 mL) and H2O (200 mL, the layers were separated and the aqueous phase extracted with CH2Cl2 (1×250 mL). The combined organic layers were washed with H2O (1×250 ML), dried (Na2SO4) and concentrated in vacuo to give the title compound as a tan solid (7.88 g, 100%) which was homogeneous by TLC and NMR. This material was used as such without purification.

Provenance & Evidence