Imidazole → tert-Butyl(2-fluorophenethoxy)dimethylsilane

HRID 1255237Notes

Reaction equation

HRID 1255237 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 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 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-a3c6229a97654a4e8dca0e8140361392
Source dataset
uspto-grants-2013_06
Patent number
US08455483B2

Reaction notes

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