3-Furancarboxylic acid, 2,5-dimethyl-, methyl ester → (2,5-Dimethylfuran-3-yl)methanol

Participants

Reaction Conditions

Reaction Steps

To a 0° C. solution of methyl 2,5-dimethyl-3-furanoate (2.0 g, 13.0 mmol) in THF (130 mL) under N2 was added lithium aluminum hydride (39 mL of a 1.0 M solution in THF, 38.9 mmol) dropwise. The reaction was stirred at 0° C. for 3.5 h, at which time it was quenched cautiously with saturated aqueous Na2SO4 solution and allowed to warm to room temperature. The reaction mixture was filtered and rinsed with ethyl acetate, the filtrate was diluted with more ethyl acetate and the layers separated. The organic layer was washed with saturated aqueous NH4Cl, water and brine and dried over Na2SO4. The solution was filtered and concentrated to afford the title compound as a clear liquid (1.54 g, 12.2 mmol, 94%). 1H NMR (300 MHz, DMSO-d6): δ 5.93 (s, 1H); 4.18 (s, 2H); 2.17 (s, 3H); 2.15 (s, 3H).

Provenance & Evidence