Methyl chloroformate → Dimethyl Cyclohexane-1,1-dicarboxylate

A solution of methyl cyclohexanecarboxylic acid (2.0 g, 14.06 mmol) in THF (5 mL) was added dropwise to a solution of lithium diisopropylamine (2.28 g, 21.1 mmol) in THF (20 mL) at −78° C. After stirring for 1 h at the same temperature, a solution of methylchloroformate (2.0 g, 21.1 mmol) in THF (5 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 (20 mL). THF was removed in vacuo and the aqueous residue was extracted with EtOAc (50 mL×3). 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 (80:20) yielded the title compound (2.8 g, 99%). MH+201.

1. customAfter 18 h the reaction mixture was quenched with saturated aqueous NH4Cl solution (20 mL)
2. customTHF was removed in vacuo
3. extractionthe aqueous residue was extracted with EtOAc (50 mL×3)
4. dry with materialThe combined organic layers were dried (MgSO4)
5. customAfter removal of the solvent
6. customunder reduced pressure, purification by flash column chromatography

ORD record

ord-7ac2a2d2c9324c12a0c2530fcbf826a5

Source dataset

uspto-grants-2008_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07332485B2