Magnesium → HCID 178447760, compound

HRID 1080580Notes

Reaction equation

HRID 1080580 reaction equation
Br[CH2:2][CH2:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[C:18]([F:27])[CH:17]=3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1.[Mg].Cl[Si:30]1([CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1>C1COCC1>[CH2:36]([Si@H:30]1[CH2:31][CH2:32][C@H:33]([CH2:2][CH2:3][C@H:4]2[CH2:9][CH2:8][C@H:7]([C:10]3[CH:15]=[CH:14][C:13]([C:16]4[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[C:18]([F:27])[CH:17]=4)=[CH:12][CH:11]=3)[CH2:6][CH2:5]2)[CH2:34][CH2:35]1)[CH2:37][CH2:38][CH2:39][CH3:40]

Participants

5

Reactant 3

HCID 5462224MagnesiumHCID 23364864HCID 23364864, compoundHCID 178505434HCID 178505434, compound

Product 1

HCID 178447760HCID 178447760, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

44.5 g (0.1 mol) of 4-(trans-4-(2-bromoethyl)cyclohexyl)-3'-fluoro-4'-trifluoromethoxybiphenyl was dripped into a mixture of 2.5 g (0.11 mol) of magnesium and 300 ml of THF to obtain a Grignard's reagent. This solution was then dripped into a 500 ml THF solution of 20.5 g (0.1 mol) of 1-chloro-1-n-pentyl-silacyclohexane. After a conventional after treatment, 4-(trans-4-(2-(trans-4-n-pentyl-4-silacyclohexyl)ethyl)cyclohexyl)-3'-fluoro-4'-trifluoromethoxybiphenyl was obtained. The silacyclohexane rings of the product were a mixture of trans isomers and cis isomers. They were separated by means of chromatography to obtain 44.9 g (yield 84.1%) of the trans isomer.

Workup

  1. customto obtain a Grignard's reagent

Sources & evidence

ORD record
ord-8da998d5c1a1429f877490df9f5899da
Source dataset
uspto-grants-1996_12
Patent number
US05582764

Reaction notes

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