Diisobutylaluminumhydride → Methyl 1-formylcyclohexane-1-carboxylate

Participants

Reaction Steps

To a solution of dimethyl cycloheptane-1,1-dicarboxylate (7.62 g, 35.6 mmol) in diethyl ether (250 mL) at −78° C. under an argon atmosphere was added diisobutylaluminum hydride (1.5M in toluene, 48 mL, 72 mmol) dropwise. After 1.5 h, the reaction mixture was quenched with a mixutre of methanol (100 mL) and water (100 mL), was filtered through Celite@ and was extracted with diethyl ether (100 mL×3). The combined organic extracts were dried (MgSO4), were filtered and were evaporated in vacuo to yield the title compound which was used without further purification. MH+185.

Provenance & Evidence