Ethanol → HCID 23293688, compound

Participants

Reaction Steps

To a suspension of NaH (1.59 g, 63.1 mmol) in 200 mL THF was added diethyl malonate (10.0 g, 62.4 mmol) gradually. The reaction mixture was stirred for 1 hr at room temperature. 3-(3-Fluorophenyl)acrylic acid ethyl ester (2-1) (11.1 g, 57.2 mmol; prepared via standard procedures from 3-fluorocinnamic acid) and EtOH (5 mL) are added. The mixture was then stirred at 90° C. for 12 hr, concentrated under diminished pressure and treated with 50 mL 10% sodium hydrogencarbonate solution. The aqueous mixture was extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried (Na2SO4). After solvent removal, the residue was purified using silica gel flash chromatography (6:1 hexane/EtOAc) to give 2-2 as an oil.

Provenance & Evidence