Diethyl 3-hydroxycyclobutane-1,1-dicarboxylate → Diethyl 3-oxocyclobutane-1,1-dicarboxylate

Participants

Reaction Steps

To a solution of diethyl 3-hydroxycyclobutane-1,1-dicarboxylate (159) (649 mg, 3 mmol) in DCM (7 mL) was added PCC (1.37 g, 6.3 mmol) and the mixture was stirred for 4 hours at room temperature. The product was filtered through a silica gel plug and the residue was purified using column chromatography with hexanes/ethyl acetate as eluent to yield diethyl 3-oxocyclobutane-1,1-dicarboxylate (160). 1H NMR (400 MHz, CD2Cl2) δ 4.28 (q, J=7.2 Hz, 4H), 3.63 (s, 4H), 1.31 (t, J=7.2 Hz, 6H). MS m/z 215.1 (M+1)+.

Provenance & Evidence