Hydrochloric Acid → HCID 57445527, compound

Participants

Reaction Steps

To a suspension of NaH (0.82 g, 20.5 mmol) in THF (40 ml), a solution of ethyl 4-hydroxy-3-iodo-benzoate (5.0 g, 17.1 mmol) in THF (40 ml), then 15-crown-5 (4.0 ml, 25.6 mmol) and finally a solution of 4-phenylbut-2-enyl bromide (5.41 g, 25.6 mmol) in THF (50 ml) were added subsequently at 0° C. The reaction mixture was kept under stirring at room temperature for 10 minutes and then warmed to 50° C. for 6 h. After equilibration at room temperature, 3 N HCl was added (30 ml) and the mixture poured into a separatory funnel. The organic layer was separated and the aqueous layer extracted with ethyl acetate (3×30 ml). The collected organic layers were washed with saturated aqueous sodium chloride and dried over sodium sulfate. The solvent was eliminated with a rotary evaporator. The residue was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate=95/5) affording 5.94 g of the title compound (82% yield).

Provenance & Evidence