Magnesium → HCID 178447759, compound

HRID 1080583Notes

Reaction equation

HRID 1080583 reaction equation
Br[CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH3:23])=[C:17]([F:24])[CH:16]=3)=[CH:11][CH:10]=2)[CH2:5][CH2:4]1.[Mg].Br[CH2:27][C@H:28]1[CH2:33][CH2:32][Si@H:31]([CH2:34][CH2:35][CH2:36][CH:37]=[CH2:38])[CH2:30][CH2:29]1>[Cu]I.P(OCC)(OCC)(OCC)=O.C1COCC1>[CH2:34]([Si@H:31]1[CH2:30][CH2:29][C@H:28]([CH2:27][CH2:2][C@H:3]2[CH2:8][CH2:7][C@H:6]([C:9]3[CH:14]=[CH:13][C:12]([C:15]4[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH3:23])=[C:17]([F:24])[CH:16]=4)=[CH:11][CH:10]=3)[CH2:5][CH2:4]2)[CH2:33][CH2:32]1)[CH2:35][CH2:36][CH:37]=[CH2:38]

Participants

7

Reactant 3

HCID 5462224MagnesiumHCID 178447740HCID 178447740, compoundHCID 178466081HCID 178466081, compound

Product 1

HCID 178447759HCID 178447759, compoundYield 71.3%

Reagents, catalysts & solvents 3

HCID 6535Triethyl PhosphateCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

39.1 g (0.1 mol) of 4-(trans-4-bromomethylcyclohexyl)-3'-fluoro-4'-ethoxybiphenyl 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 0.5 g of triethyl phosphate, 0.1 g of copper (I) iodide and 26.1 g (0.1 mol) of trans-1-bromomethyl-4-(4-pentenyl)-4-silacyclohexane. After a conventional after treatment, purification was conducted by means of chromatography to obtain 35.1 g (yield 71.3%) of 4-(trans-4-(2-(trans-4-(4-pentenyl)-4-silacyclohexyl)ethyl)cyclohexyl)-3'-fluoro-4'-ethoxybiphenyl.

Workup

  1. customto obtain a Grignard's reagent
  2. customAfter a conventional after treatment, purification

Sources & evidence

ORD record
ord-9d848bd52086465d8dadab4360d2746a
Source dataset
uspto-grants-1996_12
Patent number
US05582764

Reaction notes

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