N,N,N',N'-Tetramethylethylenediamine → 1,4-Dimethoxy-2,5-bis(methoxymethoxy)-3-methylthiobenzene

Participants

Reaction Conditions

Reaction Steps

259 Milligrams of 1,4-dimethoxy-2,5-bis(methoxymethoxy)benzene was dissolved in a mixed solvent of 12 ml of toluene with 3 ml of hexamethylphosphoric triamide, to this solution was added 0.303 ml of N,N,N',N'-tetramethylethylenediamine, then the whole mixture was cooled to -78° C. in a dry ice-acetone bath. Next, 1.34 ml of n-butyllithium (1.6 mole hexane solution ) was added dropwise to the reaction mixture and stirred for 20 minutes. Further, 0.14 ml of dimethyl disulfide was added dropwise and stirred for additional 2 hours. The reaction mixture was warmed to room temperature, 30 ml of diethyl ether was added, then the organic layer was washed three times with 20 ml of water, further washed three times with 20 ml of a saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate. Then this solution was concentrated under reduced pressure, and the residue obtained was purified by thin layer chromatography (thickness 2 mm, silica gel, solvent: 40% ethyl acetate-n-hexane solution) to yield 152 mg of 1,4-dimethoxy-2,5-bis(methoxymethoxy)-3-methylthiobenzene. Colorless oily substance.

Provenance & Evidence