Imidazole → tert-Butyl(5-ethyl-2-fluorophenoxy)dimethylsilane

HRID 2105012Notes

Reaction equation

HRID 2105012 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([F:10])=[C:7]([OH:9])[CH:8]=1)[CH3:2].N1C=CN=C1.[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]>CN(C=O)C>[C:19]([Si:16]([O:9][C:7]1[CH:8]=[C:3]([CH2:1][CH3:2])[CH:4]=[CH:5][C:6]=1[F:10])([CH3:18])[CH3:17])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 187116495-Ethyl-2-fluorophenol

Product 1

HCID 59838026tert-Butyl(5-ethyl-2-fluorophenoxy)dimethylsilaneYield 505.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Intermediate 188.1 (5.42 g, 38.7 mmol) in 25 mL DMF at rt, were added imidazole (2.90 g, 42.5 mmol) and TBS-Cl (5.83 mmol). The mixture was stirred for 1.5 h, then was diluted with hexanes. The organic phase was washed with H2O (3×) and brine, dried (Na2SO4), then concentrated. Purification by flash chromatography (100% hexanes) afforded 7.50 g of Intermediate 188.2 as a colorless oil.

Workup

  1. washThe organic phase was washed with H2O (3×) and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customPurification by flash chromatography (100% hexanes)

Sources & evidence

ORD record
ord-529f2bbbaede4f63a262664e022f7fcc
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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