Triethylamine → Difluoro-acetic acid 4-(4-ethylcyclohexyl)-cyclohexyl ester

Participants

Reaction Conditions

Reaction Steps

In 30 ml of dichloromethane were dissolved 2.2 g (11 mmol) of 4-(4-ethylcyclohexyl)cyclohexanol, 1.9 g (20 mmol) of difluoroacetic acid, and 0.8 g (8 mmol) of triethylamine, and this solution was cooled down to 0° C. To this solution was added dropwise 15 ml of solution of 2.4 g (12 mmol) of dicyclohexylcarbodiimide (DCC) in dichloromethane, and the mixture was stirred at the same temperature for 1 hour and then at room temperature for 17 hours. After the crystals in the suspension thus obtained were filtered off, the solvent was distilled off under a reduced pressure. After the residue was purified by column chromatography on silica gel (eluent: heptane/toluene=1/1), the solvent was distilled off, and the residue was subjected twice to recrystallization to give 1.4 g (4.9 mmol) of difluoro-acetic acid 4-(4-ethylcyclohexyl)-cyclohexyl ester. Yield of this compound based on 4-(4-ethylcyclohexyl)cyclohexanol was 45%.

Provenance & Evidence