Ethyl bromoacetate → HCID 58460212, compound

Participants

Reaction Conditions

Reaction Steps

n-Butyl lithium (101 mL, 161 mmol) was added to a stirred solution of diisopropylamine (22.96 mL) in methyl-THF (200 mL) at −10° C. The resulting solution was stirred at −10° C. for 15 mins. 1,2-cyclohexanedione (8.6 g) was added to the reaction mixture as a solution in methyl-THF (28 mL). During the addition the internal temperature of the reaction was maintained between −15° C. and −5° C. by modulation of delivery rate. The resulting dark orange/brown solution was stirred at −10° C. for a further 15 mins. The reaction mixture was then cooled to −78° C. and ethyl bromoacetate (12.76 mL) was added dropwise via syringe. Further ethyl bromoacetate (0.8 mL) was added, no further evolution of heat was observed therefore the reaction was left to stir at −60 to −70° C. (internal temp) for 1 hour 15 minutes. The reaction mixture was quenched at −78° C. with 0.5 M HCl (400 ml), allowed to warm to RT and extracted with diethyl ether (200 ml). The organic layer was washed with water (300 mL) and saturated brine. The crude reaction mixture was purified by flash column chromatography (100 g, silica, ethyl acetate/cyclohexane, 0-50%) to give the title compound (7.1 g). LC/MS MH+ 199, Rt 1.78 mins (5 min system).

Provenance & Evidence