4-(4-Phenyl-4-n-propyl-4-silacyclohexyl)cyclohexanone → 4-(4-(4-Fluorophenyl)-3-cyclohexenyl)-1-phenyl-1-n-propyl-1-silacyclohexane

HRID 439631

Reaction equation

HRID 439631 reaction equation
[CH2:1]([Si:4]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:9][CH2:8][CH:7]([CH:10]2[CH2:15][CH2:14][C:13](=O)[CH2:12][CH2:11]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].[F:23][C:24]1[CH:29]=[CH:28][C:27]([Mg]Cl)=[CH:26][CH:25]=1>>[CH2:1]([Si:4]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:9][CH2:8][CH:7]([CH:10]2[CH2:15][CH2:14][C:13]([C:27]3[CH:28]=[CH:29][C:24]([F:23])=[CH:25][CH:26]=3)=[CH:12][CH2:11]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3]

Participants

3

Reactant 2

HCID 110343904-(4-Phenyl-4-n-propyl-4-silacyclohexyl)cyclohexanoneHCID 178505844HCID 178505844, compound

Product 1

HCID 110146944-(4-(4-Fluorophenyl)-3-cyclohexenyl)-1-phenyl-1-n-propyl-1-silacyclohexaneYield 82%

Procedure

In the same manner as in Example 1, 35.0 g of 4-(4-n-propyl-4-phenyl-4-silacyclohexyl)cyclohexanone were subjected to coupling reaction with 4-fluorophenylmagnesium chloride, followed by dehydration reaction in the presence of an acid catalyst to obtain 35.9 g of 4-(4-n-propyl-4-phenyl-4-silacyclohexyl)-1-(4-fluorophenyl)-1-cyclohexene (yield: 82%). The results of 1H-NMR analysis are shown below. 1H-NMR (CDCl3) δ:0.50-2.55 (23H, m), 5.90-6.14 (1H, m), 6.80-7.65 (9H, ppm

Workup

  1. customfollowed by dehydration reaction in the presence of an acid catalyst

Sources & evidence

ORD record
ord-c1ad0bce64464ad4b2e00e75591c42e0
Source dataset
uspto-grants-1996_05
Patent number
US05514824

Linked notes

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