1-Bromopropane → HCID 178460936, compound

HRID 1080575Notes

Reaction equation

HRID 1080575 reaction equation
[CH3:1][CH2:2][CH2:3]Br.[Mg].Cl[SiH:7]1[CH2:12][CH2:11][CH:10]([CH2:13][CH2:14][C@H:15]2[CH2:20][CH2:19][C@H:18]([C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[CH:29][CH:28]=4)=[CH:23][CH:22]=3)[CH2:17][CH2:16]2)[CH2:9][CH2:8]1>C1COCC1>[CH2:3]([Si@H:7]1[CH2:12][CH2:11][C@H:10]([CH2:13][CH2:14][C@H:15]2[CH2:16][CH2:17][C@H:18]([C:21]3[CH:22]=[CH:23][C:24]([C:27]4[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[CH:29][CH:28]=4)=[CH:25][CH:26]=3)[CH2:19][CH2:20]2)[CH2:9][CH2:8]1)[CH2:2][CH3:1]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 5462224MagnesiumHCID 178509564HCID 178509564, compound

Product 1

HCID 178460936HCID 178460936, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

12.5 g (0.1 mol) of n-propyl bromide was dripped into a mixture of 2.5 g (0.1 mol) of magnesium and 500 ml of THF to obtain a Grignard's reagent. This solution was then dripped into a 300 ml THF solution of 42 g (0.1 mol) of 4-(trans-4-(2-(4-chloro-4-silacyclohexyl)ethyl)cyclohexyl)-4'-cyanobiphenyl to obtain 4-(trans-4-(2-(trans-4-n-propyl-4-silacyclohexyl)ethyl)cyclohexyl)-4'-cyanobiphenyl. The silacyclohexane rings of the product were a mixture of trans isomers and cis isomers. They were separated by means of chromatography to obtain 32.8 g (yield 76.4%) of the trans isomer.

Workup

  1. customto obtain a Grignard's reagent

Sources & evidence

ORD record
ord-adf09db95cfb4ee2ae418fafc3ae7d5d
Source dataset
uspto-grants-1996_12
Patent number
US05582764

Reaction notes

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