Hydrochloric Acid → HCID 178455728, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3.68 g of 1-bromomethyl-4-ethynylcyclohexane (trans/cis=about 3/1) in 20 mL of N,N-dimethylformamide were added 3.13 g of 3,3,3-trifluoropropylmalononitrile, 3.21 g of potassium iodide and 2.67 g of potassium carbonate, followed by stirring at 70° C. for 5 hours. The reaction mixture was cooled to room temperature and then 50 mL of a 1 N aqueous hydrochloric acid solution was added thereto. The reaction mixture was extracted three times with 30 mL of ethyl acetate. The combined organic layer was washed sequentially with 100 mL of a saturated aqueous sodium hydrogen carbonate solution and 100 mL of a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 3.20 g of the trans isomer (hereinafter referred to as the present compound (1t)) and 1.01 g of the cis isomer (hereinafter referred to as the present compound (1c)) of 1-(2,2-dicyano-5,5,5-trifluoropentyl)-4-ethynylcyclohexane (hereinafter referred to as the present compound (1)) represented by the following formula:

Provenance & Evidence