Methanol → 5-(2-Benzyloxyethyl)-6-methyl-1,3-benzodioxole

Participants

Reaction Conditions

Reaction Steps

3.0 g of 5-(2-benzyloxyethyl)-6-bromo-1,3-benzodioxole was dissolved in 100 ml of anhydrous ether. 8.5 ml of a 1.6 M solution of n-butyllithium in hexane was added to the solution at -78° C. and the reaction was conducted at -50° C. for 2 h. The reaction mixture was cooled again to -78° C. 6.4 g of methyl iodide was added thereto and the temperature was gradually elevated to room temperature. Methanol and water were added to the reaction mixture. After extraction with ethyl acetate, the extract was dried over magnesium sulfate and concentrated under reduced pressure to obtain a crude methyl compound. After purification according to silica gel column chromatography (ethylacetate/hexane=2:98), 1.9 g of the intended compound was obtained in the form of a pale yellow oil.

Provenance & Evidence