Quinoline → 2-Bromomethyl-5-[1-(4-chlorophenoxy)-2-methylprop-2-yl]-5-methyl-tetrahydrofuran

Participants

Reaction Steps

16 g (0.1 mole) of bromine are added dropwise to 28.2 g (0.1 mole) of 7-(4-chlorophenoxy)-5-hydroxy-5,6,6-trimethyl-hept-1-ene in 200 ml of absolute chloroform at room temperature, with stirring, and 13 g (0.1 mole) of quinoline are then added at -10° C., with cooling. The reaction mixture is stirred at room temperature for a further 2 hours and concentrated in vacuo, the residue is taken up in ether, the mixture is filtered, the filtrate is again concentrated in vacuo and the residue is stirred in a waterbath at 95° C. for 1 hour. The resulting mixture is taken up in ether, the mixture is filtered and the filtrate is washed with 15 percent strength hydrochloric acid and then with water, dried over sodium sulphate and freed from the solvent in vacuo. 32.7 g (90% of theory) of 2-bromomethyl-5-[1-(4-chlorophenoxy)-2-methylprop-2-yl]-5-methyl-tetrahydrofuran are obtained as an oil, which can be used in the next stage without further purification. ##STR114##

Provenance & Evidence