Magnesium → HCID 178447752, compound

HRID 1080581Notes

Reaction equation

HRID 1080581 reaction equation
Br[CH2:2][C@H:3]1[CH2:8][CH2:7][Si@H:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH2:5][CH2:4]1.[Mg].I[CH2:16][C@H:17]1[CH2:22][CH2:21][C@H:20]([C:23]2[CH:28]=[CH:27][C:26]([C:29]3[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=3)=[CH:25][CH:24]=2)[CH2:19][CH2:18]1>[Cu]I.P(OCC)(OCC)(OCC)=O.C1COCC1>[CH2:9]([Si@H:6]1[CH2:7][CH2:8][C@H:3]([CH2:2][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:30]=[CH:31][C:32]([C:35]([F:36])([F:37])[F:38])=[CH:33][CH:34]=4)=[CH:25][CH:24]=3)[CH2:21][CH2:22]2)[CH2:4][CH2:5]1)[CH2:10][CH2:11][CH2:12][CH3:13]

Participants

7

Reactant 3

HCID 5462224MagnesiumHCID 178447741HCID 178447741, compoundHCID 178506110HCID 178506110, compound

Product 1

HCID 178447752HCID 178447752, compoundYield 76.9%

Reagents, catalysts & solvents 3

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

Procedure

26.3 g (0.1 mol) of trans-1-bromomethyl-4-n-pentyl-4-silacyclohexane 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 44.4 g (0.1 mol) of 4-(trans-4-iodomethylcyclohexyl)-4'-trifluoromethylbiphenyl. After a conventional after treatment, purification was conducted by means of chromatography to obtain 38.5 g (yield 76.9%) of 4-(trans-4-(2-(trans-4-n-pentyl-4-silacyclohexyl)ethyl)cyclohexyl)-4'-trifluoromethylbiphenyl was obtained.

Workup

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

Sources & evidence

ORD record
ord-3dde35b3de12431997b75e9663eb69e1
Source dataset
uspto-grants-1996_12
Patent number
US05582764

Reaction notes

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