5-(ethoxymethyl)furan-2-carbaldehyde

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 7.5 ml batch reactor, 0.06 mmol 5-(ethoxymethyl)furfural (EMF) in 1 mL ethanol and 5 bars of hydrogen was reacted with 3 mol % of a Pt/C catalyst for 4 days at room temperature. The starting material was completely converted in 100% selectivity to 5-(ethoxymethyl)-2-hydroxymethyl)furan. Subsequently, the mixture was heated to 75° C. for 1 day without hydrogen. The 5-(ethoxymethyl)-2-hydroxymethyl)furan was fully converted and 2,5-bis(ethoxymethyl)furan was obtained in 80% yield. 20% Side products are ring opened levulinate derivatives. The experiment was successfully repeated on a 20 gram scale.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. The excess ethanol was recovered by distillation the residue was chromatographed (silica gel, CH2Cl2:Et2O, 2:1)