p-Toluenesulfonic acid → 2-Tridecyl-5-(2-bromoethoxy)tetrahydrofuran

Participants

Reaction Steps

To 2 g (8 mmol) of 2-tridecyl-2,3-dihydrofuran an 1.1 g (8.8 mmol) of 2-bromo-ethanol in 50 ml of carbon tetrachloride were added 20 mg (0.1 mmol) of dry p-toluene-sulphonic acid. After stirring overnight at room temperature, the solvent was evacuated under reduced pressure. The residue was diluted with a aqueous solution of sodium carbonate and extracted with diethyl ether. The organic phase was washed with water and then dryed on anhydrous magnesium sulphate. The solvent was removed by evaporation and the residue was chromatographed on silica gel using 10% by volume diethyl ether in petroleum ether as eluent. This method allowed the recovery, as oils, of first the trans title compound (896 mg) then a mixture of both cis and trans isomers (419 mg) and, finally, the cis isomer (340 mg) as confirmed by their spectral data: NMR (250 MHz, CDCl3, TMS*) δ ##STR25##

Provenance & Evidence