Imidazole → tert-Butyl(2-fluorophenethoxy)dimethylsilane

HRID 471170

Reaction equation

HRID 471170 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-75e7c65448fb44f4b8dc805bd90d4d62
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Linked notes

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