Water → HCID 19922432, compound

Participants

Reaction Steps

To a mechanically stirred slurry of (2-methoxyphenyl)acetonitrile (10.0 g, 68 nmol ), 4-picolyl chloride hydrochloride (25.0 g, 152 nmol), and 1.2 g benzyltriethylammonium chloride in toluene (200 ml) at room temperature was added 50% NaOH (50 ml) over a period of 15 min. After addition was complete, the reaction mixture was slowly heated to 50° and maintained at that temperature for approx. 3 h. Completion of the reaction was determined by TLC. While still stirring the reaction mixture at 50°, 70 ml of water was added, and stirring was continued for 15 min. The mixture was cooled to room temperature, and the layers were separated. To the toluene layer was added 14.0 g Magnesol (an intimate mixture of silica gel and magnesium sulfate), and the solution was stirred at 50° for 30 min. The solution was filtered, and the solvent was removed under reduced pressure. The subsequent oil was purified via column chromatography (silica gel, 10% methanol/methylene chloride) to give α,α-Bis(4-pyridinylmethyl)2-methoxybenzeneacetonitrile as a solid, 16.4 g, 73% yield. NMR (200 MHz, CDCl3) δ 3.26 (d, 2H, J=13 Hz); 3.88 (d, 2H, J=13 Hz); 4.07 (s, 3H); 6.70 (m, 6H); 7.00 (m, 6H); 7.30 (m, 1H); 8.38 (m, 4H). Mass Calcd. for C21H19N3O: 329.1528. Found: 329.1505.

Provenance & Evidence