Methanol → Dimethyl 2-[4-(hydroxymethyl)benzyl]-3-isopropylmaleate

Participants

Reaction Steps

To a solution of 2-[4-(hydroxymethyl)benzyl]-3-isopropylmaleic anhydride (101 mg, 0.388 mmol) in a mixed solvent of methanol (1.0 mL) and tetrahydrofuran (1.0 mL) was added a 2.0 M trimethylsilyl diazomethane-hexane solution (1.0 mL, 2.0 mmol) with stirring under ice cooling. The reaction mixture was stirred at room temperature for 2 h and directly concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography (toluene-ethyl acetate 4:1→3:1) to give 96 mg of dimethyl 2-[4-(hydroxymethyl)benzyl]-3-isopropylmaleate as oil (yield: 81%).

Provenance & Evidence