Cesium carbonate → 5-(Oxiran-2-ylmethoxy)quinoline

Participants

Reaction Steps

297 g of cesium carbonate was added to 600 ml of dimethylformamide. Further, 83.5 g of 5-hydroxyquinoline was added. The mixture was stirred at 25°-30° C. for 30 minutes. To the reaction mixture was slowly added 109 g of glycidyl tosylate. The resulting mixture was stirred at 25°-30° C. for 15 hours. The reaction mixture was poured into 3 liters of ice water, followed by stirring and extraction with 2 liters of ethyl acetate. The aqueous layer was subjected to extraction with 2 liters of ethyl acetate. The organic layers were combined and washed twice with 2 liters of water. The ethyl acetate layer was dried over anhydrous Glauber's salt and subjected to vacuum distillation to remove the solvent. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain 76.8 g (yield: 66%) of intended 5-(2,3-epoxypropoxy)quinoline as a light yellow powder.

Provenance & Evidence