Tetrahydrofuran → 2-(4-Ethoxy-2,3-difluorophenyl)-5-pent-1-enylselenophene

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Reaction Steps

4.12 g (10.3 mmol) of butyltriphenylphosphonium bromide are initially introduced in 50 ml of THF at 0° C., and 1.04 g (9.27 mmol) of potassium tert-butoxide dissolved in 7 ml of THF are added. After 1.75 h at RT, 2.27 g (7.20 mmol) of 5-(4-ethoxy-2,3-difluorophenyl)selenophene-2-carbaldehyde are added in one portion with ice-cooling, and the batch is stirred at RT for 6 h. The mixture is diluted with MTBE, and water and 2 N hydrochloric acid are added. The organic phase is separated off, and the aqueous phase is extracted with MTBE. The combined organic phases are washed with sat. sodium chloride soln. and dried using sodium sulfate. The solution is concentrated to dryness, and the residue is purified by column chromatography (SiO2, n-heptane:EtOAc=5:1-2:1). 2-(4-Ethoxy-2,3-difluorophenyl)-5-pent-1-enylselenophene is obtained as an orange oil.

Provenance & Evidence