Triethylamine → Oct-6-en-2-one

Participants

Reaction Steps

81.3 g (0.38 mol) of 2-bromopropionyl bromide in 100 ml of hexane were added over a period of 1 hour to 39.8 g (0.5 mol) of 1,3-cyclohexadiene and 38.6 g (0.38 mol) of triethylamine while maintaining the temperature below 40° C. by occasional cooling. After an additional 3 hours at room temperature the precipitated triethylamine hydrobromide was removed by filtration. The filtrate was evaporated and the residue was purified by distillation under reduced pressure and subsequently by chromatography on silica gel using 4% diethyl ether in hexane for the elution. There were obtained 9.48 g of exo-8-bromo-8-methylbicyclo[4:2:0]oct-2-en-7-one and 5 89 g of endo-8-bromo-8-methylbicyclo[4:2:0]oct-2-en-7-one.

Provenance & Evidence