Ethyl 2-oxocyclohexanecarboxylate → Ethyl 3-(4-chlorobenzoyl)-2-oxocyclohexanecarboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of LHMDS (21 mL, 2.1 mmol) in 50 mL of anhydrous THF under a nitrogen atmosphere at −78° C. was added 2-oxo-cyclohexanecarboxylic acid ethyl ester Compound 1a (1.80 g, 10.0 mmol) in 10 mL of anhydrous THF. The resultant homogeneous mixture was left to stir at −78° C. for 40 min followed by the drop wise addition of 4-chloro-N-methoxy-N-methyl-benzamide Compound 1b (2.0 g, 10 mmol) in 10 mL of anhydrous THF. The reaction mixture was allowed to stir for 18 hours and allowed to warm to ambient temperature. The reaction mixture was quenched with water (50 mL) and the organic layer was extracted with EtOAc (200 mL) and washed with brine, separated and dried with anhydrous Na2SO4, then filtered and concentrated in vacuo to yield 3-(4-chloro-benzoyl)-2-oxo-cyclohexanecarboxylic acid ethyl ester Compound 1c (1.7 g) as an oil, which was used in the next step without further purification.

Provenance & Evidence