Methyl chloroformate → Dimethyl 4,4-dimethylcyclohexane-1,1-dicarboxylate

Participants

Reaction Steps

A solution of methyl 4,4-dimethyl-cyclohexane carboxylic acid (7.17 g, 42.2 mmol) in THF (15 mL) was added dropwise to a solution of lithium diisopropylamine (6.84 g, 63.3 mmol) in THF (60 mL) at −78° C. After stirring for 1 h at the same temperature, a solution of methylchloroformate (6.0 g, 63.3 nmol) in THF (15 mL) was added slowly and the mixture was allowed to warm to room temperature. After 18 h the reaction mixture was quenched with saturated aqueous NH4Cl solution (150 mL) and the aqueous residue was extracted with EtOAc (100 mL×5). The combined organic layers were dried (MgSO4). After removal of the solvent under reduced pressure, purification by flash column chromatography using an eluting system of hexane/EtOAc (95:5) yielded the title compound as a clear colorless liquid (5.23 g, 54%). MH+229.

Provenance & Evidence