Sulfuric Acid → HCID 12148783, compound

Participants

Reaction Steps

1.4 ml (10 mmol) diisopropylamine and 65 ml (100 mmol) 1.55 M n-BuLi solution in hexane were added under argon at −78° C. to a well-stirred suspension of 37.5 g (105 mmol) methyltriphenylphosphonium bromide in 400 ml anhydrous tetrahydrofuran (THF). The reaction mixture was allowed to heat to room temperature, cooled again and then at −78° C. a solution of 16.8 g (100 mmol) 2-(bicyclo-[3.1.0]hex-1-yl)-2-oxoacetic acid methyl ester in 20 ml THF was added dropwise so that the temperature did not exceed −50° C. The solution was then stirred for 10 hours at room temperature and acidified with 5% sulphuric acid. After the addition of 50 ml saturated sodium chloride solution the organic phase was separated off, the aqueous phase extracted with diethyl ether and the combined organic phase washed with saturated sodium chloride solution. 10 mg 2,6-di-t-butyl-p-cresol (BHT) were added for stabilizing, then the solvent was distilled off and the residue purified by column chromatography (pentane/diethyl ether 20:1). 15.7 g (85% yield) of BCHAM was obtained as colourless liquid.

Provenance & Evidence