Quinone → 2,5-Cyclohexadien-1-one, 4-hydroxy-4-(phenylethynyl)-

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Reaction Conditions

Reaction Steps

Benzoquinone (6.3 g, 0.006 mole) was dissolved in 25 mL of dry THF and placed under nitrogen. The reaction was cooled to -78° C. and the solution prepared above was added slowly. The reaction was stirred at -78° C. for 1.5 hr and quenched with ammonium chloride solution. The mixture was extracted with ether, the ether phase washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 0.91 g of a brown oil which crystallized while under vacuum. The crystals were further purified by flash column chromatography on silica using 1:4 EtOAc/hexane. The compound-bearing fractions were combined and concentrated in vacuo to yield 31% of the title 1,2-1,4 adduct.

Provenance & Evidence