Cesium carbonate → HCID 14349146, compound

Participants

Reaction Steps

A mixture of 2-chloromethyl quinoline (1.1 g; 6.3 mmol), 3-(6-phenoxy-1-hydroxyhexyl)phenol (1.8 g, 6.3 mmol) and finely powdered anhydrous potassium carbonate (1.74 g, 12.6 mmol) in acetone (40 ml) containing catalytic amounts of finely powdered, anhydrous cesium carbonate (0.4, 1.3 mmol) and sodium iodide (0.05 g, 0.33 mmol) was refluxed overnight (15 hours). The reaction mixture was cooled to the room temperature and filtered. The solid residue was washed thrroughly with acetone (3×15 ml), and all the filtrates were combined. All volatiles were removed from the combined acetone filtrate to leave a light yellow viscous liquid which solidifed to an off-white solid on trituration with a 1:1 mixture of ether and petroleum ether (35°-55° C.). This solid was chromatographed on silica gel with 35% ethylacetate in hexanes to yield the desired product (1.6 g, 60%) as a white crystalline solid, mp 83°-84.5° C.

Provenance & Evidence