Cyclohexanemethanol → Cyclohexanemethanol

Participants

Reaction Steps

A mixture of (5-(cyclohexylmethoxy)furan-2-yl)methanol and cyclohexylmethanol (0.75 g) and MnO2 (3.16 g, 36.3 mmol) in anhydrous CH2Cl2 (16 mL) was stirred at room temperature for 3 days. The reaction mixture was filtered through Celite and concentrated under reduced pressure. Flash chromatography purification (10%-50% EtOAc—hexanes gradient) gave 5-(cyclohexylmethoxy)furan-2-carbaldehyde with cyclohexylmethanol as an impurity as a light yellow. Yield (0.68 g, 99%); 1H NMR (400 MHz, DMSO-d6) δ 9.20 (s, 1H), 7.52 (d, J=3.8 Hz, 1H), 5.79 (d, J=3.8 Hz, 1H), 4.03 (d, J=5.8 Hz, 2H), 1.55-1.80 (m, 6H), 0.96-1.25 (m, 5H).

Provenance & Evidence