1-Chloropentane → HCID 178447753, compound

HRID 1080576Notes

Reaction equation

HRID 1080576 reaction equation
[CH2:1](Cl)[CH2:2][CH2:3][CH2:4][CH3:5].[Mg].Cl[SiH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][C@H:17]2[CH2:22][CH2:21][C@H:20]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([F:36])[CH:30]=4)=[CH:25][CH:24]=3)[CH2:19][CH2:18]2)[CH2:11][CH2:10]1>C1COCC1>[CH2:1]([Si@H:9]1[CH2:10][CH2:11][C@H:12]([CH2:15][CH2:16][C@H:17]2[CH2:18][CH2:19][C@H:20]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([F:36])[CH:30]=4)=[CH:25][CH:24]=3)[CH2:21][CH2:22]2)[CH2:13][CH2:14]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 109771-ChloropentaneHCID 5462224MagnesiumHCID 178505435HCID 178505435, compound

Product 1

HCID 178447753HCID 178447753, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

10.7 g (0.1 mol) of n-pentyl chloride was dripped into a mixture of 2.5 g (0.1 mol) of magnesium and 300 ml of THF to obtain a Grignard's reagent. This solution was then dripped into a 300 ml THF solution of 45 g (0.1 mol) of 4-(trans-4-(2-(4-chloro-4-silacyclohexyl)ethyl)cyclohexyl)-3'-fluoro-4'-chlorobiphenyl to obtain 4-(trans-4-(2-(trans-4-n-pentyl-4-silacyclohexyl)ethyl)cyclohexyl)-3'-fluoro-4'-chlorobiphenyl. The silacyclohexane rings of the product were a mixture of trans isomers and cis isomers. They were separated by means of chromatography to obtain 31.3 g (yield 69.9%) of the trans isomer.

Workup

  1. customto obtain a Grignard's reagent

Sources & evidence

ORD record
ord-9debecc8c5bc4c41a2f61f6376b4c27d
Source dataset
uspto-grants-1996_12
Patent number
US05582764

Reaction notes

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