Diethyl 1,1-cyclobutanedicarboxylate → Ethyl 1-(hydroxymethyl)cyclobutane-1-carboxylate

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Reaction Steps

Diethyl cyclobutane-1,1-dicarboxylate (7.17 mL) was added to a THF (150 mL) suspension of LiAH(OtBu)3 (22.08 g) at room temperature, and the suspension was refluxed for 7 h. The THF was stripped off and the mixture was quenched with water, neutralized with HCl (3 M) and extracted with dichloromethane and ethylacetate. The combined organic phases were washed with brine, dried and evaporated. The crude residue was put on a column and eluted with DCM : EtOAc; 5:1 to give ethyl 1-(hydroxymethyl)-cyclobutanecarboxylate (4.08 g) as a clear oil. 1H-NMR (300 MHz, CDCl3), δ=4.3372-4.1188 (q, 2H); 3.9337-3.7479 (d, 2H); 2.5485-2.322 (m, 3H); 2.1117-1.9015 (m, 4H); 1.3963-1.2174 (t, 3H) ppm.

Provenance & Evidence