Water → HCID 56612223, compound

Participants

Reaction Steps

4-Isopropenyl-3,7-dimethyl-6-octen-1-yn-3-ol (0.192 g; 10-3 mole) is kept at a temperature in the region of 40° C. and protected from light in the presence of silver trifluoromethanesulphonate (0.257 g; 10-3 mole) in a mixture (3:1 by volume) of tetrahydrofuran and water (10 cc). After 20 hours the reaction mixture is diluted with ethyl ether (20 cc) and treated with a saturated solution of sodium bicarbonate (5 cc). After separation, the organic phase is washed with demineralised water until neutral, and then dried over magnesium sulphate. After filtration, evaporation of the solvent under reduced pressure (20 mm Hg; 2.7 kPa) and purification by chromatography on alumina, 6,10-dimethyl-3,6,8-undecatrien-2-one (0.110 g) is obtained in a yield of 57%, having the following characteristics:

Provenance & Evidence