Hydrochloric Acid → HCID 44232484, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1.14 g of 4-(3,3-dicyano-6,6,6-trifluorohexyl)cyclohexanone in 10 mL of tetrahydrofuran was added 10 mL of a 0.5 M solution of ethynyl magnesium bromide in tetrahydrofuran at 0° C. under a nitrogen atmosphere, followed by stirring at 0° C. for 5 hours. To the reaction mixture was added 30 mL of a 1 N aqueous hydrochloric acid solution, followed by extraction twice with 30 mL of ethyl acetate. The combined organic layer was washed sequentially with 30 mL of a saturated aqueous sodium hydrogen carbonate solution and 30 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 0.78 g of 1-(3,3-dicyano-6,6,6-trifluorohexyl)-4-ethynyl-4-hydroxycyclohexane (hereinafter referred to as the present compound (6)) represented by the following formula:

Provenance & Evidence