Triethylamine → N-(2-allyl-4-fluoro-phenyl)-acrylamide

Participants

Reaction Conditions

Reaction Steps

A round-bottom flask containing the product from Step 1 (10.6 g, 70.1 mmol) was fitted with a stirbar and septa. Tetrahydrofuran (200 mL) and triethylamine (15.0 mL, 108 mmol) were added, giving a solution that was cooled to −10° C. Acryloyl chloride (6.0 mL, 73.6 mmol) was then added, and the resulting mixture was allowed to gradually warm to room temperature. After 16 hours, the reaction was concentrated to remove most of the tetrahydrofuran, then diluted with ethyl acetate (200 mL) and washed with 1:1 H2O:saturated aqueous NaCl solution (2×100 mL). The organic extracts were dried over MgSO4, filtered and concentrated in vacuo to give an oil which was purified via flash chromatography on silica gel (15% to 40% ethyl acetate/hexanes linear gradient) to give the desired product.

Provenance & Evidence