Quinone → Spiro[2.4]hept-5-ene-4,7diol Diacetate

참여 물질

반응 단계

To a two phase mixture of palladium acetate (1.7 g), lithium acetate dihydrate (123.6 g), lithium chloride (30.0 g), manganese (IV) oxide (15.3 g) and p-benzoquinone (1.4 g) in acetic acid (250 ml), water (420 ml) and pentane (3.7 l) was added spiro[2.4]hepta-4,6-diene (7.7 g) and the resulting mixture was stirred at ambient temperature for 24 hours. The reaction mixture was filtered through a celite plug washing with pentane (1 l). The organic phase was collected, washed successively with saturated sodium bicarbonate solution (500 ml), water (500 ml) and brine (100 ml) then concentrated to dryness under reduced pressure. The residue was absorbed onto silica and purified by chromatography (SiO2; 9:1 isohexane:ethyl acetate) to afford the subtitle compound (2.1 g).

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