Magnesium → HCID 178460931, compound

HRID 259876Notes

Reaction equation

HRID 259876 reaction equation
[CH:1]([Si@H:4]1[CH2:9][CH2:8][C@H:7]([CH2:10]Br)[CH2:6][CH2:5]1)=[CH:2][CH3:3].[Mg].Br[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[C:23]([F:28])[CH:22]=2)=[CH:17][CH:16]=1>C1COCC1>[CH:1]([Si@H:4]1[CH2:9][CH2:8][C@H:7]([CH2:10][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[C:23]([F:28])[CH:22]=3)=[CH:19][CH:20]=2)[CH2:6][CH2:5]1)=[CH:2][CH3:3]

Participants

5

Reactant 3

HCID 5462224MagnesiumHCID 19030246HCID 19030246, compoundHCID 178460927HCID 178460927, compound

Product 1

HCID 178460931HCID 178460931, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4.7 g (20 mmol) of trans-1-(1-propenyl)-4-bromomethyl-1-silacyclohexane was dripped into a mixture of 0.5 g (21 mmol) of magnesium and 50 ml of THF to obtain a Grignard's reagent. This solution was then dripped into a 50 ml THF solution of 5.7 g (20 mmol) of 4'-bromomethyl-3,4-difluorobiphenyl and a catalytic amount of cuprous chloride to obtain 4-[2-(trans-4-(1-propenyl)-4-silacyclohexyl) ethyl]-3',4'-difluorobiphenyl. The silacyclohexane rings of this product were a mixture of trans isomers and cis isomers. After a conventional after treatment, they were separated by means of chromatography to obtain 6.1 g of the trans isomers (yield 86%).

Workup

  1. customto obtain a Grignard's reagent

Sources & evidence

ORD record
ord-1c24564feb3643e9b1e4676ce10483c5
Source dataset
uspto-grants-1996_06
Patent number
US05523440

Reaction notes

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