4-Ethyl-4-p-tolyl-4-silacyclohexanone → 4-(4-(4-Fluorophenyl)phenyl)-1-ethyl-1-p-tolyl-1-silacyclohexane

HRID 1684446Notes

Reaction equation

HRID 1684446 reaction equation
[CH2:1]([Si:3]1([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1)[CH3:2].[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][C:27]([Mg]Br)=[CH:26][CH:25]=2)=[CH:20][CH:19]=1>>[F:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]2[CH:29]=[CH:28][C:27]([CH:6]3[CH2:7][CH2:8][Si:3]([CH2:1][CH3:2])([C:10]4[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=4)[CH2:4][CH2:5]3)=[CH:26][CH:25]=2)=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 190391564-Ethyl-4-p-tolyl-4-silacyclohexanoneHCID 178505512HCID 178505512, compound

Product 1

HCID 190391554-(4-(4-Fluorophenyl)phenyl)-1-ethyl-1-p-tolyl-1-silacyclohexane

Procedure

Using the same method as Example 14, 23.2 g of 4-ethyl-4-p-tolyl-4-silacyclohexanone was reacted with 4-(4-fluorophenyl)phenyl magnesium bromide; the alcohol generated was treated with a dehydration reaction followed by catalytic reduction to obtain 4-(4-(4-fluorophenyl)phenyl)-1-ethyl-1-p-tolyl-1-silacyclohexane; this was then reacted with iodine monochloride; and then the product was reduced using lithium aluminum hydride to obtain 2.12 g (yield 71%) of the target product.

Sources & evidence

ORD record
ord-2d59a15dab2c46cb967a87f17e8a6ddc
Source dataset
uspto-grants-1997_06
Patent number
US05641431

Reaction notes

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