Hydrochloric Acid → HCID 178447714, compound

Participants

Reaction Steps

34.1 g of 4-(4-n-pentyl-4-phenyl-4-silacyclohexyl)-3-cyclohexenone was dropped in 250 ml of a tetrahydrofuran solution of 0.5 moles of trans-(4-n-propylcyclohexyl)phenylmagnesium chloride, followed by agitation at room temperature for 5 hours. The resultant mixture was charged into diluted hydrochloric acid and extracted with ether. The resultant ether solution was washed with brine, dried and concentrated, followed by addition, to the resultant residue, of 300 ml of benzene and 800 mg of p-toluenesulfonic acid monohydrate and removal of generated water under reflux. When the generation of water stopped, the benzene solution was washed with brine, dried and concentrated, followed by purification through column chromatography to obtain 36.8 g of 1-(4-n-pentyl-4-phenyl-4-silacylohexyl)-4-(trans-4-n-propylcyclohexyl)phenyl-1,3-cyclohexadiene at a yield of 70%. The results of 1H-NMR analysis of the compound are shown below. 1H-NMR (CDCl3) δ:0.50-2.75(41H, m), 5.62-5.90(1H, m), 6.18-6.36(1H, m), 7.05-7.70(9H, m) ppm

Provenance & Evidence