Water → 3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile

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Reaction Conditions

Reaction Steps

Under nitrogen, mix together 5.4 ml (0.0382 mol) of redistilled diisopropylamine and 60 ml of THF. Cool the mixture to −50° C. and pour in dropwise 15.3 ml (0.0382 mol) of a 2.5N solution of butyllithium in hexane. Allow the temperature to rise again to −5° C. and stir for 10 minutes. Cool the solution to −60° C. and pour in dropwise a solution of 3 g (0.00954 mol) of 2-(2-cyanoethyl)-4,5-dimethoxyphenyl dimethylsulphamate in 35 ml of THF. Allow the temperature slowly to rise again to −24° C. while monitoring by HPLC disappearance of the reactant. Add the reaction mixture to a mixture of water and ice and extract with ethyl acetate. Wash the organic phases in succession with 1N sodium hydroxide solution, aqueous 1N HCl solution, water and saturated aqueous NaCl solution and then dry them over MgSO4, filter, and evaporate off the solvents. 2 g of residue are obtained which is purified by flash chromatography on 70 g of silica (eluant=dichloromethane) to yield 0.9 g of title product in the form of a white solid.

Provenance & Evidence