Boron trifluoride etherate → HCID 58963165, compound

Participants

Reaction Steps

7-Ethyl-3-methylbenzofuran-5-carbaldehyde 32 (2 g, 10.9 mmole), dry methanol (40 ml), and 4-aminobenzonitrile (1.42 g, 12 mmoles) were combined and heated to reflux under a nitrogen atmosphere. The reaction was refluxed for 2.5 hours and then cooled to room temperature. Tosylmethylisonitrile (2.12 g, 10.0 mmoles) was added with 9 ml methanol. The reaction mixture was cooled to 0° C. and BF3-OEt2 was added drop wise over 40 minutes. The reaction was allowed to stir for 2 hours and water (2 ml) was added and the reaction stirred for at least 1 hour. The solvent was removed in vacuo and the residue partitioned between ethyl acetate and aqueous citric acid. The organic layer was separated, washed with brine, dried over sodium sulfate and the solvent removed in vacuo. The crude product was purified by flash chromatography (25% ethyl acetate in hexanes) to yield 2.19 g of methyl 2-(4-cyanophenylamino)-2-(7-ethyl-3-methylbenzofuran-5-yl)acetate 5.

Provenance & Evidence