Imidazole → tert-Butyl(2-fluorophenethoxy)dimethylsilane

HRID 446361

Reaction equation

HRID 446361 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][OH:10].N1C=CN=C1.[C:16]([Si:20]([CH3:23])([CH3:22])Cl)([CH3:19])([CH3:18])[CH3:17]>CN(C=O)C>[C:16]([Si:20]([O:10][CH2:9][CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])([CH3:23])[CH3:22])([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

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

Product 1

HCID 57988979tert-Butyl(2-fluorophenethoxy)dimethylsilane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(2-fluorophenyl)ethanol (5.5 g) and imidazole (8.0 g) in DMF (50 mL) was cooled in ice-water, treated with tert-butyldimethylchlorosilane (6.52 g), then removed as from the cooling bath and stirred at room temperature for 3.5 hours. The solution was poured into water and extracted three times with diethyl ether. The combined organic extracts were washed three times with water, once with brine, then dried over anhydrous magnesium sulphate and concentrated under reduced pressure to afford the subtitled compound as a colourless oil. Yield 9.9 g.

Workup

  1. customremoved as from the cooling bath
  2. additionThe solution was poured into water
  3. extractionextracted three times with diethyl ether
  4. washThe combined organic extracts were washed three times with water
  5. dry with materialonce with brine, then dried over anhydrous magnesium sulphate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8f60e07498774f7a95a9ed9eff840734
Source dataset
uspto-grants-2013_07
Patent number
US08476265B2

Linked notes

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