Methyl chloroformate → Dimethyl 3-butylcyclobutane-1,1-dicarboxylate

Participants

Reaction Steps

A solution of 3-butyl-cyclobutanecarboxylic acid methyl ester (7.75 g, 45.6 mmol) in THF (30 mL) was added dropwise to a solution of lithium diisopropylamine (7.26 g, 68.4 mmol) in THF (70 mL) at −78° C. After stirring for 1.5 h at the same temperature, methyl chloroformate (6.46 g, 68.4 mmol) 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 (200 mL) and the aqueous residue was extracted with EtOAc (75 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 yellow oil (8.37 g, 81%). MH+229.

Provenance & Evidence