Ethanol → 5-(Ethoxymethyl)furan-2-carbaldehyde

Participants

Reaction Steps

5-(Chloromethyl)furfural (CMF, 1) (1.24 g, 8.58 mmol) was dissolved in absolute ethanol (60 mL) and the solution was stirred at room temperature for 8 h. The excess ethanol was recovered by distillation and the residue was chromatographed (silica gel, CH2Cl2:Et2O, 2:1) to give EMF (5) (1.26 g, 95%) as a pale yellow liquid, 1H NMR (CDCl3); 1.04 (t, 3H), 3.39 (q, 2H), 4.32 (s, 2H), 6.34 (d, 1H), 7.06 (d, 1H), 9.40 (s, 1H), 13C NMR (CDCl3); 14.1, 63.6, 65.3, 110.3, 121.8, 151.8, 157.9, 176.7.

Provenance & Evidence