m-Chloroperbenzoic acid → 3,4-epoxy-2,2-diethyl-3,4-dihydro-2H-1-benzopyran-6-carbonitrile

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Reaction Steps

12 g of the above chromene are dissolved in 400 ml of abs. dichloromethane, the obtained solution is mixed with anhydrous sodium bicarbonate and oxidized during 3 days with 31 mg of m-chloroperbenzoic acid. The slightly yellow suspension is partitioned between an aq. ammoniumhydroxide solution (5%) and dichlormethane, the organic phases are washed with water and dried over sodiumsulphate. The oil, obtained after concentration, is purified by flash-chromatography (silica gel/dichloromethane, hexane 2:3). Besides of educt, 2,2-diethyl-3,4-epoxy-3,4-dihydro-2H-1-benzopyran-6-carbonitrile is obtained as colorless oil.

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