Dimethyl Sulfate → 3-Methoxy-2-methyl-4H-pyran-4-one

Participants

Reaction Steps

Dimethylsulphate (3.8 ml, 5.05 g, 0.04 mmol) was added to a solution of maltol (5.0 g, 0.04 mmol) in 10% aqueous potassium hydroxide (22.5 ml). After stirring for 5h the reaction mixture was extracted into CH2Cl2 (x3). The organic extract was dried (MgSO4) and concentrated under reduced pressure. The residue was chromatographed on silica gel 60 eluting with 60% ethyl acetate in hexane to give the title compound (2.06 g, 37%) as a pale yellow oil; νmax (film) 3080, 1620, and 1580 cm-1 ; δH (CDCl3) 2.3 (3H, s), 3.8 (3H, s), 6.3 (1H, d, J 6 Hz), 7.6 (1H, d, J 6 Hz).

Provenance & Evidence