Hydrochloric Acid → HCID 19090496, compound

Participants

Reaction Steps

To a suspension of α,α-bis(4-pyridinylmethyl)-2-methoxybenzene-acetic acid (7.7 g) in dichloroethane (150 ml) at 0° was added boron tribromide-methyl sulfide complex (1M in dichloromethane, 5 equivalents, 110 mmol, 110 ml). The mixture was warmed to room temperature, then heated at reflux for 20 h. After cooling to room temperature, 6N HCl (100 ml) was added, and the mixture was refluxed for 18 h. The mixture was cooled, diluted with water, and the layers were separated. The organic layer was extracted twice with 1N HCl (50 ml each). The combined aqueous layer was basified to pH 9 with concentrated ammonium hydroxide, and extracted with dichloromethane. The organic solution was dried over magnesium sulfate, filtered, and evaporated to give an oil. Purification by column chromatography (silica gel/3% methanol in dichloromethane) afforded 3,3-bis(pyridinylmethyl)-2(3H)benzofuranone [(4.7 g, 14.9 mmol, 68%) NMR (200 MHz, CDCl3) δ 3.31 (dd, 4H); 6.75 (m, 1H); 6.82 (dd, 4H); 7.14-7.30 (m, 3H); 8.35 (dd, 4H). Mass Calcd. for C20H16N2O2 : 316.1211. Found: 316.1202] and unreacted α,α-bis(4-pyridinylmethyl)-2-methoxybenzene-acetic acid (2.5 g, 7.2 mmol).

Provenance & Evidence