Dimethyl Cyclohexane-1,1-dicarboxylate → Methyl 1-formylcyclohexane-1-carboxylate

Participants

Reaction Steps

To a solution of dimethyl cyclohexane-1,1-dicarboxylate (2.8 g, 14.0 mmol) in dichloromethane(55 mL) at −78° C. under a nitrogen atmosphere was added diisobutylaluminum hydride (1.5M in toluene, 19 mL, 28 mmol) dropwise. After 3 h, the reaction mixture was quenched with saturated aqueous NH4Cl solution (11 mL), then 1N HCl (14 mL) and allowed to warm to room temperature. The mixture was filtered through Celite@ and the organic phase was separated, was dried (MgSO4) and was evaporated in vacuo to yield the title compound which was used without further purification (1.23 g, 52%). MH+171.

Provenance & Evidence