Silane, (chloromethyl)trimethyl- → 2,6-Diethyl-4-[2-(trimethylsilyl)ethyl]phenol

HRID 466306Notes

Reaction equation

HRID 466306 reaction equation
[Mg].Cl[CH2:3][Si:4]([CH3:7])([CH3:6])[CH3:5].Br[CH2:9][C:10]1[CH:15]=[C:14]([CH2:16][CH3:17])[C:13]([OH:18])=[C:12]([CH2:19][CH3:20])[CH:11]=1>C(OCC)C>[CH2:19]([C:12]1[CH:11]=[C:10]([CH2:9][CH2:3][Si:4]([CH3:7])([CH3:6])[CH3:5])[CH:15]=[C:14]([CH2:16][CH3:17])[C:13]=1[OH:18])[CH3:20]

Participants

5

Reactant 3

HCID 75361Silane, (chloromethyl)trimethyl-HCID 5462224Magnesium2×HCID 232970944-Bromomethyl-2,6-diethylphenol

Product 1

HCID 152944442,6-Diethyl-4-[2-(trimethylsilyl)ethyl]phenol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

Mix magnesium turnings (240 mg, 10 mmol) and anhydrous ethyl ether under an inert atmosphere. Add a solution of chloromethyltrimethylsilane (1.9 g, 10 mmol) in anhydrous ethyl ether. Stir until the magnesium metal dissolves. Add a solution of 4-bromomethyl-2,6-diethylphenol (2.43 g, 10 mmol) in anhydrous ethyl ether and reflux the mixture until the reaction is complete. Pour onto a mixture of ice/hydrochloric acid and separate the layers. Wash the ethereal layer with water, dry (MgSO4) and evaporate to give the title compound which is purified by silica gel chromatography.

Workup

  1. dissolutiondissolves
  2. temperaturereflux the mixture until the reaction
  3. customseparate the layers
  4. washWash the ethereal layer with water
  5. dry with materialdry (MgSO4)
  6. customevaporate

Sources & evidence

ORD record
ord-5bbdef80b8964dcdbc7e632717cbfdcd
Source dataset
uspto-grants-1992_10
Patent number
US05155250

Reaction notes

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