Methyl iodide → 5-(2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl)-3-methoxy-6-methyl-2-cyclohexen-1-one

Participants

Reaction Conditions

Reaction Steps

To a -78° C. solution of 0.5 mole of lithiodiisopropylamide in 500 ml of tetrahydrofuran (from 50.5 g, 0.5 mole diisopropylamine and 417 ml of 1.2 M n-butyllithium in hexane) is added dropwise (30 mm) a solution of 217 g (0.5 mole) of 5-(2-benzyloxy-4-(1,1-dimethylheptyl)phenyl)-3-methoxy-2-cyclohexen-1-one in 250 ml of tetrahydrofuran. The reaction is stirred 30 minutes longer at -78° C. followed by the addition of 179 g (1.0 mole) of hexamethylphosphoramide and 78.1 g (0.55 mole) of methyl iodide. The reaction is allowed to slowly warm to room temperature, stirred one hour and quenched by the addition of 10 ml of water. The reaction is evaporated under reduced pressure to remove the tetrahydrofuran and added to one liter ice water-one liter ether. The ether extract is washed with three one liter portions of water, dried over magnesium sulfate and evaporated to yield the title compound in nearly pure form. The title compound is purified via column chromatography on 2 kg of silica gel eluted with ether-pentane.

Provenance & Evidence