Diethyl 3-(benzyloxy)cyclobutane-1,1-dicarboxylate → Diethyl 3-hydroxycyclobutane-1,1-dicarboxylate

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Reaction Steps

To a solution of diethyl 3-(benzyloxy)cyclobutane-1,1-dicarboxylate (158) (1.43 g, 4.7 mmol) in EtOH (18 mL) was added 10% palladium on carbon (143 mg) and the mixture was hydrogenated with a H2 balloon for 12 hours at room temperature. The catalyst was removed by filtration using celite, washed with ethyl acetate and EtOH and the solvent was removed under reduced pressure. The crude product was purified via column chromatography using hexanes/ethyl acetate as eluent to yield diethyl 3-hydroxycyclobutane-1,1-dicarboxylate (159). 1H NMR (400 MHz, CD2Cl2) δ 4.4-4.32 (m, 1H), 4.21 (qd, J=7.2, 2.0 Hz, 4H), 2.89-2.84 (m, 2H), 2.46-2.41 (m, 2H), 2.20 (d, J=6.4 Hz, 1H), 1.27 (t, J=7.2 Hz, 6H). MS m/z 217.1 (M+1)+.

Provenance & Evidence