Methyl iodide → HCID 12819456, compound

Participants

Reaction Steps

Methyl α-methylthio[m-(5,5-dimethyl-2-phenyl-1,3-dioxa-2-cyclohexyl)phenyl]acetate (406 mg) was dissolved in 3 ml of anhydrous dimethyl sulfoxide. Sodium hydride (50 mg; 65% content) was added, and the mixture was stirred for 15 minutes at room temperature. The mixture turned into a reddish brown solution with the evolution of hydrogen. When 0.15 ml of methyl iodide was added to the solution, its color vanished. The mixture was stirred for an additional 10 minutes at room temperature. An aqueous solution of ammonium chloride (0.2 g/30 ml) was added, and the mixture was extracted three times with 20 ml of diethyl ether. The organic layer was washed twice with 10 ml of water, dried over anhydrous sodium and concentrated under reduced pressure. The residue was chromatographed on a column of Florisil using benzene and diethyl ether as eluents to afford 368 mg of methyl α-methylthio-α-[m-(5,5-dimethyl-2-phenyl-1,3-dioxa-2-cyclohexyl)phenyl]propionate as a colorless oily substance in a yield of 87%.

Provenance & Evidence