Hydrochloric Acid → Ethyl 2-methyl-2-(4-nitrophenyl)propanoate

Participants

Reaction Conditions

Reaction Steps

A 250 mL oven-dried flask capped with a rubber septum was evacuated and backfilled with argon. The flask was charged with NaH (7.26 g, 181 mmol, 60% dispersion in oil) anhydrous dimethylformamide (50 mL) and the flask was cooled to 0° C. Ethyl 2-chloropropionate (10.0 g, 73.2 mmol) and nitrobenzene (9.92 g, 80.5 mmol) were dissolved in anhydrous dimethylformamide (50 mL) and added dropwise to the sodium hydride slurry. The reaction was stirred for 30 min at 0° C., the cooling bath removed and the reaction was allowed to reach ambient temperature. After 1 h iodomethane (10.4 g, 73.2 mmol) was added and the mixture was stirred for an additional 30 min. The contents of the flask were poured into a mixture of ice and 1N HCl followed by three extractions with dichloromethane. The combined organic layers were washed five times with water, three times with saturated aqueous sodium bicarbonate solution, dried over sodium sulfate, filtered and concentrated in vacuo. Purification was performed by silica gel flash chromatography eluting with a gradient of hexanes and dichloromethane (30% hexanes in dichloromethane to 100% dichloromethane) to yield ethyl 2-methyl-2-(4-nitrophenyl)propanoate (7.32 g, 42.2%).

Provenance & Evidence