1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → HCID 90410801, compound

Participants

Reaction Steps

DMTCl (0.79 g, 2.34 mmol) was added to a stirred solution of 46 (0.5 g, 1.96 mmol) in 20 ml of anhydrous pyridine. After being stirred at room temperature overnight the reaction was quenched with MeOH (2 ml) and concentrated to an oil. The oil was partition between dichloromethane and 10% citric acid. The organic phase was washed with saturated NaCl, dried over Na2SO4 and concentrated. The resulting material was chromatographed on silica eluting with a gradient of methanol (5-7.5%) in ethyl acetate. Concentration of the pure product fractions afforded 0.99 g (90%) of 47 as a white amorphous solid. 1H NMR (DMSO-d6): δ 10.78 (s, 1H), 7.73 (d, J=7 Hz, 1H), 7.27 (m, 5H), 7.16 (m, 4H), 6.98 (d, J=7 Hz, 1H), 6.82 (m, 4H), 4.60 (d, J=5 Hz, 1H), 3.84 (d, J=7 Hz, 2H), 3.76 (m, 1H), 3.72 (s, 6H), 3.08 (m, 1H), 2.99 (m, 1H), 2.20 (m, 1H), 2.09 (s, 3H), 1.03 (d, J=6 Hz, 3H).

Provenance & Evidence