Selectfluor → Ethyl 2-fluoro-3-(furan-2-yl)-3-oxopropanoate

Participants

Reaction Steps

Following the method of Banks et al. (J. Chem. Soc., Chem. Commun. 1994, 343), to a stirred solution of 10.0 g (54.9 mmol) ethyl beta-oxo-2-furanpropionate in 500 ml acetonitrile at room temperature was added 19.4 g (54.9 mmol) 1-chloromethyl-4-fluoro-1,4-diazonia-bicyclo[2.2.2]octane bis(tetrafluoroborate) and stirring continued for 90 hours at room temperature. The reaction mixture was concentrated in vacuo and the residue resuspended in ether and washed sequentially with water and with brine. The organic phase was then dried over sodium sulfate and concentrated in vacuo to afford 8.72 g (79%) (RS)-2-fluoro-3-furan-2-yl-3-oxo-propionic acid ethyl ester as a yellow oil which was used in the next step without further purification. EI-MS m/e (%): 200 (M+, 8), 155 ([M—OEt]+, 4), 95 (100).

Provenance & Evidence