Hydrochloric Acid → 4-(4-Tert-butylphenyl)-6-methyl-1,2,3,5-tetrahydro-s-indacene

반응식

[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:22]3[CH2:21][CH2:20][CH2:19][C:18]=3[CH:17]=[C:16]3[C:12]=2[CH2:13][CH:14]([CH3:24])[C:15]3=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>C(OCC)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:12]3[CH2:13][C:14]([CH3:24])=[CH:15][C:16]=3[CH:17]=[C:18]3[C:22]=2[CH2:21][CH2:20][CH2:19]3)=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

실험 절차

10 g (0.031 mol) of 4-(4-tert-butylphenyl)-2-methyl-3,5,6,7-tetrahydro-s-indacen-1(2H)-one (1c) were added dropwise at 0° C. to a solution of 0.6 g (0.016 mol) of lithium aluminum hydride in 100 ml of diethyl ether. The reaction mixture obtained was warmed to room temperature and stirred for a further one hour. 50 ml of 5% strength hydrochloric acid were added. The organic phase was separated off, washed twice with water and dried over magnesium sulfate. The residue was dissolved in 200 ml of benzene and, after addition of 0.5 g of p-toluenesulfonic acid, refluxed for 15 minutes. The solution was cooled to room temperature, washed with a 5% strength solution of sodium hydrogencarbonate and dried over magnesium sulfate. Evaporation of the solvent gave pure 4-(4-tert-butylphenyl)-6-methyl-1,2,3,5-tetrahydro-s-indacene in quantitative yield.