Hydrochloric Acid → methyl (S)-3-benzyloxymethyloxy-2-methylpropionate

Participants

Reaction Steps

Methyl (S)-(+)-2-methyl-3-hydroxypropionate (2.0 g; 16.9 mmole) and diisopropylethylamine (2.2 g; 17.1 mmole) were dissolved in dry dichloromethane (2 ml), and benzyloxymethyl chloride (2.7 g; 17.3 mmole) was dropwise added thereto, followed by stirring for 1 hour. 1N Hydrochloric acid (10 ml) and ethyl acetate (20 ml) were added thereto, and the aqueous layer was extracted with ethyl acetate. The extract was combined with the organic layer, washed with a sodium bicarbonate solution and water and dried over anhydrous magnesium sulfate. After removal of the solvent under reduced pressure, the residue was purified by silica gel column chromatography to give methyl (S)-3-benzyloxymethyloxy-2-methylpropionate.

Provenance & Evidence