Isopropanol → HCID 178505736, compound

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.

1. additionwas added to the solution at room temperature
2. temperatureunder reflux for 1 hour
3. concentrationThe resultant solution was concentrated
4. additionafter which 200 ml of hexane was added
5. customThe hydrochloride was removed by filtration
6. concentrationthe resultant filtrate was concentrated
7. customto obtain
8. distillationThis mixture was subjected to distillation under reduced pressure
9. customto remove the acetophenone
10. dissolutionthe residue was dissolved in 100 ml of THF
11. additionadded to a solution of 10.0 g of lithium aluminium hydride in 100 ml of THF
12. temperatureunder reflux for 1 hour
13. additionafter which the mixture was poured into 200 ml of 5% hydrochloric acid
14. extractionextracted with ethyl acetate
15. extractionThe resultant extract
16. washwas washed with brine
17. customdried
18. concentrationconcentrated by a usual manner
19. customfollowed by purification through silica gel chromatography

ORD record

ord-9dc9b6f61a5c43f599509d3df10797a1

Source dataset

uspto-grants-1996_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05523439