Diethyl Malonate → HCID 67099760, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-methyl-2-(4-(trifluoromethyl)phenyl)propanoic acid (1325 mg, 5706 μmol) in thionyl chloride (4162 μL, 57063 μmol) was heated at reflux under nitrogen. After 2 hours, the reaction was cooled to 23° C. and concentrated in vacuo to afford the crude acid chloride. In an oven-dried round-bottomed flask, magnesium (208 mg, 8559 μmol) and diethyl malonate (1293 μL, 8559 μmol) were added to EtOH (15 mL) and CCl4 (0.2 mL). The reaction was stirred at 23° C. for 30 minutes followed by the addition of THF (15 mL). The reaction was heated to reflux under nitrogen. After 1 hour, a solution of the crude acid chloride in THF (10 mL) was added in a drop wise fashion. After 30 minutes, the reaction was cooled to 23° C., diluted with diethyl ether (150 mL), and washed with water (150 mL). The aqueous layer was extracted with diethyl ether (150 mL). The combined ether layers were washed with brine (100 mL), dried over MgSO4, concentrated in vacuo, and purified on silica gel (eluant: 5-20% EtOAc/hexane) affording 1115 mg of the title compound. MS m/e=375.2 (M+H)+.

Provenance & Evidence