Imidazole → tert-Butyl(4-fluorophenethoxy)dimethylsilane

HRID 1255232Notes

Reaction equation

HRID 1255232 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 (9.03 g) was added portionwise to a stirred solution of 2-(4-fluorophenyl)ethanol (7 g) and imidazole (4.08 g) in DMF (100 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, filtered and the solvent concentrated under reduced pressure. The crude product was purified by flash silica chromatography eluting with 2% ethyl acetate in isohexane. Fractions containing the product were evaporated to dryness to afford the subtitled compound. Yield 11.60 g.

Workup

  1. custompartitioned between ethyl acetate and brine
  2. washThe organic layer was washed twice with brine
  3. customdried
  4. filtrationfiltered
  5. concentrationthe solvent concentrated under reduced pressure
  6. customThe crude product was purified by flash silica chromatography
  7. washeluting with 2% ethyl acetate in isohexane
  8. additionFractions containing the product
  9. customwere evaporated to dryness

Sources & evidence

ORD record
ord-37a456827cd544fdbbaa5b60170b587c
Source dataset
uspto-grants-2013_06
Patent number
US08455483B2

Reaction notes

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