Pyridine → HCID 11425515, compound

Participants

Reaction Steps

To a flask containing of dichloromethane (58 ml) was added powdered 4 A sieves (3.37 g, activated at 500° C. for 8 h), phenylboronic acid (3.53 g, 28.95 mmol), 3-chloro-4-hydroxy-5-methoxybenzaldehyde (1.08 g, 5.79 mmol), copper (II) acetate (1.05 g, 5.79 mmol), pyridine (2.33 ml, 28.95 mmol) and triethylamine (4.0 ml, 28.95 mmol). The reaction flask was fitted with a drying tube and stirred overnight at room temperature. Filtration through celite and removal of volatiles in vacuo followed by column chromatography (silica, 10% ethyl acetate in hexane) provided the title compound as a yellow solid (540 mg, 35%). 1H NMR (400 MHz, CDCl3) δ 9.93 (s, 1H), 7.60 (s, 1H), 7.44 (s, 1H), 7.28 (t, j=8.0 Hz, 2H), 7.05 (t, j=7.2 Hz, 1H), 6.83 (d, j=8.4 Hz, 2H), 3.84 (s, 3H). M+1=263

Provenance & Evidence