Diethyl Ether → HCID 58002946, compound

Participants

Reaction Conditions

Reaction Steps

Under argon, 25 g of visnagin (108.6 mmol) are suspended in 500 ml of abs. diethyl ether and 50 ml of abs. tetrahydrofuran, 2.23 g (8.7 mmol) of nickel(II) acetylacetonate are added and the mixture is cooled to −20° C. At this temperature, 81.44 ml (162.9 mmol) of trimethylaluminum (2 M solution in hexane) are added slowly, and the mixture is then slowly warmed to 0° C. and stirring is continued. After one hour, 500 ml of saturated potassium/sodium tartrate solution are added (vigorous evolution of gas), and the mixture is then diluted with 500 ml of ethyl acetate. The organic phase is separated off and the aqueous phase is extracted once more with ethyl acetate. The combined organic phases are washed twice with saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated to dryness. The residue is chromatographed on silica gel (mobile phase: cyclohexane/ethyl acetate 5:1). This gives 23.28 g (86% of theory) of the title compound.

Provenance & Evidence