Acetic Acid → HCID 11034458, compound

Participants

Reaction Steps

88.5 g (0.5 mol) of N-bromosuccinimide and 30 g (0.5 mol) of glacial acetic acid in 1.1 liter of THF are added dropwise at 0°, over a period of 8 hours, to a solution of 60 g (0.23 mol) of 6-cyclohexyl-2(S)-isopropyl-4-hexenoic acid dimethylamide in 1.4 liters of THF/H2O (2:1). When the addition is complete, the reaction mixture is stirred for 30 minutes at 0°, then poured onto 1.8 liters of ice-cold 40% sodium hydrogen sulphite solution. The aqueous phase is extracted three times with ether and the combined organic phases are washed in succession with 1N HCl, saturated NaHCO3 solution and brine. After drying with MgSO4 and evaporating off the solvent, the residue is chromatographed over silica gel with hexane/ether (2:1) and again concentrated. The residue is recrystallised from hexane, m.p. 95°-95.5°.

Provenance & Evidence