Imidazole → tert-Butyl(4-fluorophenethoxy)dimethylsilane

HRID 1689458Notes

Reaction equation

HRID 1689458 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][C:13]([CH2:16][CH2:17][OH:18])=[CH:12][CH:11]=1.N1C=CN=C1>CN(C=O)C>[C:4]([Si:1]([O:18][CH2:17][CH2:16][C:13]1[CH:14]=[CH:15][C:10]([F:9])=[CH:11][CH:12]=1)([CH3:3])[CH3:2])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 820684-Fluorophenethyl Alcohol

Product 1

HCID 57989254tert-Butyl(4-fluorophenethoxy)dimethylsilane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyldimethylsilyl chloride (0.903 g) was added portionwise to a stirred solution of 2-(4-fluorophenyl)ethanol (0.7 g) and imidazole (0.408 g) in DMF (20 mL) at 20° C. The reaction mixture was stirred for 3 hours at room temperature and then partitioned between ethyl acetate and brine. The organic layer was washed twice with brine, dried over sodium sulphate, filtered and the solvent evaporated under reduced pressure. The crude product was purified by flash silica chromatography using 2% ethyl acetate in isohexane as solvent. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 0.99 g.

Workup

  1. custompartitioned between ethyl acetate and brine
  2. washThe organic layer was washed twice with brine
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure
  6. customThe crude product was purified by flash silica chromatography
  7. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-2f2cae46b5a746b6b738f9ee2aaeb036
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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