2,6-Dichlorobenzaldehyde → HCID 86602771, compound

Participants

Reaction Steps

To a stirred solution at room temperature of III (150 mg, 0.42 mmol), 2,6-dichlorobenzaldehyde (148 mg, 0.85 mmol) or aldehyde (1.5–2.0 equiv.) in MeOH (10 ml) was added a solution of NaOH (1.7 ml, 1N in H2O). A pale yellow precipitate appeared. After 3 days, the reaction mixture was filtered off, rinsed with H2O. The solid residue was then dissolved in AcOEt, dried over anhydrous MgSO4, filtered and concentrated. The crude residue was finally purified by flash chromatography on silica gel (AcOEt/hexane:20/80→40/60) to afford the title compound IVc (185 mg, 0.36 mmol, 85% yield) as a pale yellow foam. 1H NMR (300 MHz, CDCl3) δ(ppm): 9.48 (bs, 1H), 8.11 (s, 4H), 7.96 (d, J=17.1 Hz, 1H), 7.89 (d, J=8.8 Hz, 1H), 7.68 (d, J=16.3 Hz, 1H), 7.42 (d, J=7.9 Hz, 2H), 7.35–7.15 (m, 4H), 6.68 (s, 1H), 1.54 (s, 9H).

Provenance & Evidence