Imidazole → tert-Butyl(2-fluorophenethoxy)dimethylsilane

HRID 1689400Notes

Reaction equation

HRID 1689400 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][CH2:17][OH:18].N1C=CN=C1>CN(C=O)C.C(OCC)(=O)C>[C:4]([Si:1]([O:18][CH2:17][CH2:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[F:9])([CH3:3])[CH3:2])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 27332962-(2-Fluorophenyl)ethan-1-ol

Product 1

HCID 57988979tert-Butyl(2-fluorophenethoxy)dimethylsilane

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyldimethylsilyl chloride (6.45 g) was added to a stirred solution of 2-(2-fluorophenyl)ethanol (5.00 g) and 1H-imidazole (7.29 g) in dry DMF (30 mL) cooled in an ice bath. After 45 min, the reaction mixture was diluted with ethyl acetate, washed three times with water and evaporated in vacuo. The resulting gum was dissolved in isohexane and applied to a silica gel column eluting with isohexane followed by 1:3 ethyl acetate:isohexane to collect the product as an oil. Yield 9.0 g.

Workup

  1. temperaturecooled in an ice bath
  2. washwashed three times with water
  3. customevaporated in vacuo
  4. dissolutionThe resulting gum was dissolved in isohexane
  5. washeluting with isohexane
  6. customisohexane to collect the product as an oil

Sources & evidence

ORD record
ord-3d902e224dd64981b808f2089e4fc9ef
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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