Magnesium → HCID 178460938, compound

HRID 1080582Notes

Reaction equation

HRID 1080582 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][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:5][CH2:4]1.[Mg].Br[CH2:28][C@H:29]1[CH2:34][CH2:33][Si@H:32]([CH2:35][CH2:36][CH3:37])[CH2:31][CH2:30]1>[Cu]I.P(OCC)(OCC)(OCC)=O.C1COCC1>[CH2:35]([Si@H:32]1[CH2:33][CH2:34][C@H:29]([CH2:28][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][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=4)=[CH:11][CH:10]=3)[CH2:5][CH2:4]2)[CH2:30][CH2:31]1)[CH2:36][CH3:37]

Participants

7

Reactant 3

HCID 5462224MagnesiumHCID 178460928HCID 178460928, compoundHCID 178506360HCID 178506360, compound

Product 1

HCID 178460938HCID 178460938, compoundYield 88%

Reagents, catalysts & solvents 3

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

Procedure

39.7 g (0.1 mol) of 4-(trans-4-bromomethylcyclohexyl)-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 0.5 g of triethyl phosphate, 0.1 g of copper (I) iodide and 23.5 g (0.1 mol) of trans-1-bromomethyl-4-n-propyl-4-silacyclohexane. After a conventional after treatment, purification was conducted by means of chromatography to obtain 43.0 g (yield 88.0%) of 4-(trans-4-(2-(trans-4-n-propyl-4-silacyclohexyl)ethyl)cyclohexyl)-4'-trifluoromethoxybiphenyl was obtained.

Workup

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

Sources & evidence

ORD record
ord-bcdf0d45cd5a41a58b4cd6ddd05264ce
Source dataset
uspto-grants-1996_12
Patent number
US05582764

Reaction notes

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