Ethyl 1-(hydroxymethyl)cyclobutane-1-carboxylate → Ethyl 1-formylcyclobutanecarboxylate

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Reaction Steps

To a dichloromethane (250 mL) solution of ethyl 1-(hydroxymethyl)cyclobutanecarboxylate (12 g) at room temperature, was added a mixture of pyridinium chlorochromate (PCC) (24.5 g) and 20 g SiO2. After 17.5 h, the organic solvent was decanted, and more dichloromethane and ethylacetate were added to wash the SiO2. The combined organic phases were concentrated, the residue and the SiO2 used in the reaction were loaded onto a column and eluted with EtOAc/DCM, 0-17%, to afford ethyl 1-formylcyclobutanecarboxylate (10.2 g) as a clear oil 1H-NMR (300 MHz, CDCl3): δ=9.76 (s, 1H); 4.32-4.0751 (d, 2H); 2.7145-2.2827 (t, 4H); 2.1954-1.6632 (m, 2H); 1.4254-1.0664(t, 3H) ppm. 13C-NMR (75 MHz, CDCl3) δ=196.96, 171.7, 61.54, 57.2, 25.95, 15.64, 14.17 ppm.

Provenance & Evidence