Dimethyl cyclopentane-1,1-dicarboxylate → Methyl 1-formylcyclopentanecarboxylate

Participants

Reaction Steps

To a solution of dimethyl cyclopentane-1,1-dicarboxylate (7.1 g, 38.1 mmol) in dichloromethane(75 mL) at −78° C. under an nitrogen atmosphere was added diisobutylaluminum hydride (1.5M in toluene, 51 mL, 76 mmol) dropwise. After 4 h, the reaction mixture was quenched with saturated aqueous NH4Cl solution (30 mL), then 1N HCl (38 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 (3.1 g, 52%). MH+157.

Provenance & Evidence