Diethyl Malonate → Diethyl 2-cyclohexylmethylmalonate

Participants

Reaction Conditions

Reaction Steps

A solution comprised of sodium (6.9 g, 0.3 mmol) in ethanol (250 mL) was treated sequentially with diethyl malonate (53.127 g, 0.3 mol) and then cyclohexylmethyl bromide (46 mL, 0.33 mol) at ambient temperature. The mixture was heated to 70° C. and stirred for approximately 12 hours. The mixture was cooled and solvent was removed by evaporation. The residue was diluted with ice water and the dilution was extracted with ethyl acetate (4×). The combined extracts were washed with water (4×) and brine, dried (MgSO4) and concentrated to provide diethyl 2-cyclohexylmethylmalonate.

Provenance & Evidence