Benzyl Alcohol → 2-(Benzyloxy)-4,6-dichloro-1,3,5-triazine

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Reaction Steps

First, a synthesis method of the hydroxy group-protecting agent 3 will be explained. An activated molecular sieve 4A, 54.1 μL (0.525 m mol) of benzyl alcohol, 118.9 mg (0.600 m mol) of 1,10-phenanthroline hydrate, 1.00 mL of dichloromethane, 92.2 mg (0,500 m mol) of cyanuric chloride were added to a test tube, and reacted at 0 degree under a nitrogen atmosphere for 5 hours. After the reaction, a precipitate was filtered, and 20 mL of ethyl acetate was added to the filtrate, which was washed with 10 mL of an aqueous solution of saturated sodium hydrogen carbonate, 5 mL of water, 10 mL of 1 N hydrochloric acid, 5 mL of water and 10 mL of saturated salt water. A resulting organic phase was dried by magnesium sulfate, from which ethyl acetate was distilled away, and the residue was isolated and purified by silica-gel chromatography to obtain 58.9 mg of 6-benzyloxy-2,4-dichloro-1,3,5-triazine (yield: 46%).

Provenance & Evidence