Isopropanol → HCID 178505736, compound

Participants

Reaction Steps

A solution, in 100 ml of dichloromethane, of 42.0 g of 4-(trans-4-(3,4-difluorophenyl)cyclohexyl)-1,1-diphenyl-1-silacyclohexane obtained in Preparatory Example 1 was added to 250 ml of a dichloromethane solution of 1.0 mol/liter of iodine monochloride at room temperature, followed by agitation for 1 hour to obtain 4-(trans-4-(3,4-difluorophenyl)cyclohexyl)-1,1-dichloro-1-silacyclohexane. Subsequently, a mixture of 50.0 g of isopropyl alcohol and 300 g of triethylamine was added to the solution at room temperature, followed by agitation under reflux for 1 hour. The resultant solution was concentrated, after which 200 ml of hexane was added thereby permitting secondarily produced hydrochloride to be settled down. The hydrochloride was removed by filtration and the resultant filtrate was concentrated to obtain a mixture of 4-(trans-4-(3,4-difluorophenyl)cyclohexyl)-1,1-diisopropoxy-1-silacyclohexane and acetophenone. This mixture was subjected to distillation under reduced pressure to remove the acetophenone therefrom, and the residue was dissolved in 100 ml of THF and added to a solution of 10.0 g of lithium aluminium hydride in 100 ml of THF. The reaction mixture was agitated under reflux for 1 hour, after which the mixture was poured into 200 ml of 5% hydrochloric acid and extracted with ethyl acetate. The resultant extract was washed with brine, dried and concentrated by a usual manner, followed by purification through silica gel chromatography to obtain 26.2 g of 4-(trans-4-(3,4-difluorophenyl)cyclohexyl)-1-silacyclohexane. The results of IR analysis of the product are shown below.

Provenance & Evidence