Hydrochloric Acid → HCID 178444313, compound

Participants

Reaction Steps

6.75 ml (10.80 mmol) of 1.6 molar n-butyllithium solution in n-hexane are added dropwise at 0° C. to 2.48 g of 1-ethynyl-4-(trans-4-pentylcyclohexyl)benzene in 25 ml of tetrahydrofuran. After 1 hour, this solution is saturated with formaldehyde, acidified by means of aqueous hydrochloric acid and partitioned between ether and water, and the organic phase is dried and evaporated. Chromatography on silica gel using n-hexane/dichloromethane (1:2) gives 1.80 g of 1-(hydroxymethylethynyl)-4-(trans-4-pentylcyclohexyl)benzene, ##STR7## which is stirred for 2 hours at room temperature with 1.05 g (6.49 mmol) of diethylaminosulfur trifluoride in 10 ml of dichloromethane. After partitioning between water and dichloromethane, the organic phase is dried over sodium sulfate, evaporated and chromatographed on silica gel using n-heptane, giving 0.94 g of 1-(fluoromethylethynyl)-4-(trans-4-pentylcyclohexyl)benzene. ##STR8##

Provenance & Evidence