Oxygen → SJ-3366

Participants

Reaction Steps

480 mg of 60% sodium hydride (12.0 mmol) was slowly added to 2.83 g of 5-ethyl-6-(α-cyano-3,5-dimethylbenzyl)-2,4-pyrimidinedione (10.0 mmol) dissolved in 50 ml of dimethyl formamide, and the mixture was stirred at room temperature for one hour. Then, to the resulting solution, 5.07 g of (cyclopent-3-en-1-yl)methyl para-toluenesulfonate (20.0 mmol) was added and stirred with injecting oxygen at 50˜60° C. for 48 hours. After cooling, 200 ml of distilled water was added to the resulting product, and extracted with 200 ml of ethyl acetate (2 ×). The obtained extract was dried with anhydrous magnesium sulfate and concentrated under the reduced pressure. Then, the concentrated residue was separated and purified with column chromatography (hexane:ethyl acetate=2:1) to obtain 2.52 g of the titled compound as a white solid.

Provenance & Evidence